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

HRID 1374572Notes

Reaction equation

HRID 1374572 reaction equation
[CH:1]1([CH2:4][N:5]2[C:11](=[O:12])[C@@H:10]([NH:13][C:14](=[O:18])[C@@H:15]([OH:17])[CH3:16])[C:9]3[CH:19]=[CH:20][CH:21]=[CH:22][C:8]=3[C:7]3[CH:23]=[CH:24][CH:25]=[CH:26][C:6]2=3)[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1)=[O:35].C(OC(=O)C)C.C1CCCCC1>ClCCl>[N+:43]([C:40]1[CH:39]=[CH:38][C:37]([O:36][C:34](=[O:35])[O:17][C@H:15]([C:14](=[O:18])[NH:13][C@@H:10]2[C:11](=[O:12])[N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6]3[CH:26]=[CH:25][CH:24]=[CH:23][C:7]=3[C:8]3[CH:22]=[CH:21][CH:20]=[CH:19][C:9]2=3)[CH3:16])=[CH:42][CH:41]=1)([O-:45])=[O:44]

Participants

6

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 21867204Cyclohexane ethylacetateHCID 69507471(S)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-hydroxy-propionamide

Product 1

HCID 86597454carbonic acid (S)-1-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester 4-nitro-phenyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.46 g (1.32 mmol) (S)—N—((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-hydroxy-propionamide in 15 ml dichloromethane were stirred with 213 μl (2.64 mmol) pyridine and 0.33 g (1.58 mmol) 4-nitrophenyl chloroformate at room temperature overnight. Chromatography on silicagel with ethylacetate/cyclohexane (0-100/100-0) gave 0.63 mg (92%) carbonic acid (S)-1-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester 4-nitro-phenyl ester as a white foam; MS: m/e: 516.5 (M+H+), [α] 589=−164° (0.94% in MeOH).

Sources & evidence

ORD record
ord-e886765c20bd4374b50bb766ccb12569
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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