methyl (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate

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

Procedure: To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 165 mg, 0.84 mmol) and (3S,2R)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester (Preparation 21, 175 mg, 0.84 mmol) in DMF (10 mL)was added HOBt (125 mg, 0.92 mmol), DIPEA (0.29 mL, 1.68 mmol) and EDCI (177 mg, 0.92 mmol) and the reaction stirred at rt for 72 h. The reaction solvent was removed in vacuo, and the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97) to give the title compound as a yellow solid. δH (CD3OD): 2.97–3.12 (2H, m), 3.67 (1H, s), 4.25 (1H, d), 4.70–4.75 (1H, m), 7.08 (1H, s), 7.15–7.21 (1H, m), 7.25–7.34 (4H, m), 7.65 (1H, s), 8.55 (1H, s); m/z (ES+)=388 [M+H]+. The reaction solvent was removed in vacuo the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL) The combined organic fractions were dried (MgSO4) concentrated in vacuo the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97)

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

Procedure: To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 165 mg, 0.84 mmol) and (3S,2R)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester (Preparation 21, 175 mg, 0.84 mmol) in DMF (10 mL)was added HOBt (125 mg, 0.92 mmol), DIPEA (0.29 mL, 1.68 mmol) and EDCI (177 mg, 0.92 mmol) and the reaction stirred at rt for 72 h. The reaction solvent was removed in vacuo, and the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97) to give the title compound as a yellow solid. δH (CD3OD): 2.97–3.12 (2H, m), 3.67 (1H, s), 4.25 (1H, d), 4.70–4.75 (1H, m), 7.08 (1H, s), 7.15–7.21 (1H, m), 7.25–7.34 (4H, m), 7.65 (1H, s), 8.55 (1H, s); m/z (ES+)=388 [M+H]+. The reaction solvent was removed in vacuo the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL) The combined organic fractions were dried (MgSO4) concentrated in vacuo the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97)

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

Procedure: To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 165 mg, 0.84 mmol) and (3S,2R)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester (Preparation 21, 175 mg, 0.84 mmol) in DMF (10 mL) was added HOBt (125 mg, 0.92 mmol), DIPEA (0.29 mL, 1.68 mmol) and EDCI (177 mg, 0.92 mmol) and the reaction stirred at rt for 72 h. The reaction solvent was removed in vacuo, and the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97) to give the title compound as a yellow solid. δH (CD3OD): 2.97-3.12 (2H, m), 3.67 (1H, s), 4.25 (1H, d), 4.70-4.75 (1H, m), 7.08 (1H, s), 7.15-7.21 (1H, m), 7.25-7.34 (4H, m), 7.65 (1H, s), 8.55 (1H, s); m/z (ES+)=388 [M+H]+. The reaction solvent was removed in vacuo the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL) The combined organic fractions were dried (MgSO4) concentrated in vacuo the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97)

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

Procedure: To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 165 mg, 0.84 mmol) and (3S,2R)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester (Preparation 21, 175 mg, 0.84 mmol) in DMF (10 mL)was added HOBt (125 mg, 0.92 mmol), DIPEA (0.29 mL, 1.68 mmol) and EDCI (177 mg, 0.92 mmol) and the reaction stirred at rt for 72 h. The reaction solvent was removed in vacuo, and the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97) to give the title compound as a yellow solid. δH (CD3OD): 2.97–3.12 (2H, m), 3.67 (1H, s), 4.25 (1H, d), 4.70–4.75 (1H, m), 7.08 (1H, s), 7.15–7.21 (1H, m), 7.25–7.34 (4H, m), 7.65 (1H, s), 8.55 (1H, s); m/z (ES+)=388 [M+H]+. The reaction solvent was removed in vacuo the residue partitioned between water (40 mL) and ethyl acetate (3×40 mL) The combined organic fractions were dried (MgSO4) concentrated in vacuo the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97)