Pyridine → HCID 67076789, compound

HRID 1348603Notes

Reaction equation

HRID 1348603 reaction equation
[OH:1][C@@H:2]([CH3:19])[C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][C@@H:7]1[CH3:18])=[O:4].N1C=CC=CC=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:28]>ClCCl>[N+:36]([C:33]1[CH:32]=[CH:31][C:30]([O:29][C:27](=[O:28])[O:1][C@H:2]([C:3](=[O:4])[NH:5][C@@H:6]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8][C@@H:7]2[CH3:18])[CH3:19])=[CH:35][CH:34]=1)([O-:38])=[O:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 67076902HCID 67076902, compound

Product 1

HCID 67076789HCID 67076789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 290 mg (1.1 mmol) of (S)-2-hydroxy-N-((6R,7S)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-propionamide and 0.177 ml (2.19 mmol) of pyridine in 10 ml of dichloromethane was treated with 274 mg (1.32 mmol) of 4-nitrophenyl chloroformate and stirred overnight at room temperature. The solvent was removed by distillation and the crude product was purified by flash-chromatography on silica gel using an ascending gradient of ethyl acetate in heptane as the eluent to yield 220 mg (47% of theory) of the title compound as a white solid, MS m/e (%): 430.3 (M+H+, 100).

Workup

  1. customThe solvent was removed by distillation
  2. customthe crude product was purified by flash-chromatography on silica gel using an ascending gradient of ethyl acetate in heptane as the eluent

Sources & evidence

ORD record
ord-451d08ec23b3462cbf534173c4b69333
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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