Pyridine → carbonic acid 4-nitro-phenyl ester (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester

HRID 1374569Notes

Reaction equation

HRID 1374569 reaction equation
[OH:1][C@@H:2]([CH3:22])[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[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]1=2)=[O:4].N1C=CC=CC=1.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31].C(OC(=O)C)C.C1CCCCC1>ClCCl>[O:13]=[C:12]1[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[C@@H:6]1[NH:5][C:3]([C@@H:2]([O:1][C:30](=[O:31])[O:32][C:33]1[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=1)[CH3:22])=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 21867204Cyclohexane ethylacetateHCID 69507451(S)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide

Product 1

HCID 86597453carbonic acid 4-nitro-phenyl ester (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.17 g (0.57 mmol) (S)-2-hydroxy-N—((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide in 5 ml dichloromethane were stirred with 93 μl (1.15 mmol) pyridine and 0.14 g (0.69 mmol) 4-nitrophenyl chloroformate at room temperature overnight. Chromatography on silicagel with ethylacetate/cyclohexane (0-100/100-0) gave 0.27 mg (75%) carbonic acid 4-nitro-phenyl ester (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester as white solid; MS: m/e: 462.3 (M+H+).

Sources & evidence

ORD record
ord-f3b319346fcf412d843081a3bf478e89
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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