1,1,1,3,3,3-hexadeuteriopropan-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL round bottomed flask, a mixture of formic acid (413 mg, 8.99 mmol) and N,N-dimethyl acetamide (30 mg, 0.09 mmol) was added to a stirred solution of chlorosulfonyl isocyanate (0.77 mL, 8.91 mmol) in dichloromethane (5 mL) at 42° C. The mixture was placed under reflux for 15 min and then cooled to ambient temperature. The resulting mixture was added to a stirred solution of 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (346 mgs, 0.90 mmol) in N,N-dimethyl acetamide (6 mL) at ambient temperature. The mixture was then stirred for 17 h and then poured onto water (15 mL). Ethyl acetate (30 mL) was added to the mixture and the phases were partitioned. The organic phase was washed with water (12 mL) (×2), dried (Na2SO4) and concentrated to furnish a pale yellow oil (385 mg, yield not determined). 1H NMR (Acetone d6, 500 MHz) inter alia δ 8.07 (d, J=9 Hz, 2H), 7.53-7.47 (m, 3H), 6.84 (d, J=9 Hz, 2 H), 5.53 (d, J=9 Hz, 1 H), 5.22-5.17 (m, 1H), 4.77-4.68 (m, 1H), 2.37 (s, 3 H) and 1.46 (d, J=6 Hz, 3 H). under reflux for 15 min poured onto water (15 mL) the phases were partitioned The organic phase was washed with water (12 mL) (×2) dried (Na2SO4) concentrated to furnish a pale yellow oil (385 mg yield not

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL round bottomed flask, a mixture of formic acid (413 mg, 8.99 mmol) and N,N-dimethyl acetamide (30 mg, 0.09 mmol) was added to a stirred solution of chlorosulfonyl isocyanate (0.77 mL, 8.91 mmol) in dichloromethane (5 mL) at 42° C. The mixture was placed under reflux for 15 min and then cooled to ambient temperature. The resulting mixture was added to a stirred solution of 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (346 mgs, 0.90 mmol) in N,N-dimethyl acetamide (6 mL) at ambient temperature. The mixture was then stirred for 17 h and then poured onto water (15 mL). Ethyl acetate (30 mL) was added to the mixture and the phases were partitioned. The organic phase was washed with water (12 mL) (×2), dried (Na2SO4) and concentrated to furnish a pale yellow oil (385 mg, yield not determined). 1H NMR (Acetone d6, 500 MHz) inter alia δ 8.07 (d, J=9 Hz, 2H), 7.53-7.47 (m, 3H), 6.84 (d, J=9 Hz, 2 H), 5.53 (d, J=9 Hz, 1 H), 5.22-5.17 (m, 1H), 4.77-4.68 (m, 1H), 2.37 (s, 3 H) and 1.46 (d, J=6 Hz, 3 H). under reflux for 15 min poured onto water (15 mL) the phases were partitioned The organic phase was washed with water (12 mL) (×2) dried (Na2SO4) concentrated to furnish a pale yellow oil (385 mg yield not

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL round bottomed flask, a mixture of formic acid (413 mg, 8.99 mmol) and N,N-dimethyl acetamide (30 mg, 0.09 mmol) was added to a stirred solution of chlorosulfonyl isocyanate (0.77 mL, 8.91 mmol) in dichloromethane (5 mL) at 42° C. The mixture was placed under reflux for 15 min and then cooled to ambient temperature. The resulting mixture was added to a stirred solution of 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (346 mgs, 0.90 mmol) in N,N-dimethyl acetamide (6 mL) at ambient temperature. The mixture was then stirred for 17 h and then poured onto water (15 mL). Ethyl acetate (30 mL) was added to the mixture and the phases were partitioned. The organic phase was washed with water (12 mL) (×2), dried (Na2SO4) and concentrated to furnish a pale yellow oil (385 mg, yield not determined). 1H NMR (Acetone d6, 500 MHz) inter alia δ 8.07 (d, J=9 Hz, 2H), 7.53-7.47 (m, 3H), 6.84 (d, J=9 Hz, 2H), 5.53 (d, J=9 Hz, 1H), 5.22-5.17 (m, 1H), 4.77-4.68 (m, 1H), 2.37 (s, 3H) and 1.46 (d, J=6 Hz, 3H). under reflux for 15 min poured onto water (15 mL) the phases were partitioned The organic phase was washed with water (12 mL) (×2) dried (Na2SO4) concentrated to furnish a pale yellow oil (385 mg yield not

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1,1-Tris(4-hydroxyphenyl)ethane was acetylated with acetic anhydride as in the example above. A white solid was obtained in 97% yield, MP=169° C. NMR (1H, d-6 acetone)--7.06(q), 2.28(s), 2.24(s), 13C NMR (d-6 acetone)--169.65, 149, 146.19, 129.75, 120.98, 51.45, 30.61, 20.91. A white solid was obtained in 97% yield, MP=169° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1,1-Tris(4-hydroxyphenyl)ethane was acetylated with acetic anhydride as in the example above. A white solid was obtained in 97% yield, MP=169° C. NMR (1H, d-6 acetone)--7.06(q), 2.28(s), 2.24(s), 13C NMR (d-6 acetone)--169.65, 149, 146.19, 129.75, 120.98, 51.45, 30.61, 20.91. A white solid was obtained in 97% yield, MP=169° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1,1-Tris(4-hydroxyphenyl)ethane was acetylated with acetic anhydride as in the example above. A white solid was obtained in 97% yield, MP=169° C. NMR (1H, d-6 acetone)--7.06(q), 2.28(s), 2.24(s), 13C NMR (d-6 acetone)--169.65, 149, 146.19, 129.75, 120.98, 51.45, 30.61, 20.91. A white solid was obtained in 97% yield, MP=169° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared from sodium cephalothin and N,N-dimethyl-5-mercapto-1H-tetrazol-1-ylacetamide as described in example 12(b) in 44.1% yield; t.l.c. (SiO2 ; B.A.W; 12:3:5) Rf=0.35; λmax (95% ethanol) 271 nm (ε 8,390); δ(free acid) [(CD3)2CO] 2.33 and 3.27 (6H, 2×s -N(CH3)2), 3.85 (2H,s, C2 methylene), 4.00 (2H,s, --CH2CO--), 4.47 (2H,bs, --CH2S--), 5.20 (1H,d, J 5 Hz, C6 proton), 5.55 (2H,s, --CH2CON(CH3)2), 5.97 (1H,dd, J 5 and 9 Hz, C7 proton), 6.9-8.0 (4H,m, thienyl protons and --CO2H), 8.29 (1H,d, J 9 Hz, --CONH--).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL round bottomed flask, a mixture of formic acid (413 mg, 8.99 mmol) and N,N-dimethyl acetamide (30 mg, 0.09 mmol) was added to a stirred solution of chlorosulfonyl isocyanate (0.77 mL, 8.91 mmol) in dichloromethane (5 mL) at 42° C. The mixture was placed under reflux for 15 min and then cooled to ambient temperature. The resulting mixture was added to a stirred solution of 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (346 mgs, 0.90 mmol) in N,N-dimethyl acetamide (6 mL) at ambient temperature. The mixture was then stirred for 17 h and then poured onto water (15 mL). Ethyl acetate (30 mL) was added to the mixture and the phases were partitioned. The organic phase was washed with water (12 mL) (×2), dried (Na2SO4) and concentrated to furnish a pale yellow oil (385 mg, yield not determined). 1H NMR (Acetone d6, 500 MHz) inter alia δ 8.07 (d, J=9 Hz, 2H), 7.53-7.47 (m, 3H), 6.84 (d, J=9 Hz, 2 H), 5.53 (d, J=9 Hz, 1 H), 5.22-5.17 (m, 1H), 4.77-4.68 (m, 1H), 2.37 (s, 3 H) and 1.46 (d, J=6 Hz, 3 H). under reflux for 15 min poured onto water (15 mL) the phases were partitioned The organic phase was washed with water (12 mL) (×2) dried (Na2SO4) concentrated to furnish a pale yellow oil (385 mg yield not