2,2,3,3,3-Pentafluoropropylamine → (2,2,3,3,3-Pentafluoro-propyl)-carbamic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester

HRID 31002

Reaction equation

HRID 31002 reaction equation
[N+](C1C=CC([O:10][C:11](=O)[O:12][C@H:13]([C:15](=[O:43])[NH:16][C@@H:17]2[C:23](=[O:24])[N:22]([CH2:25][CH2:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:21]3[CH:35]=[CH:36][CH:37]=[CH:38][C:20]=3[C:19]3[CH:39]=[CH:40][CH:41]=[CH:42][C:18]2=3)[CH3:14])=CC=1)([O-])=O.[F:45][C:46]([F:53])([C:49]([F:52])([F:51])[F:50])[CH2:47][NH2:48]>>[CH2:28]([O:27][CH2:26][CH2:25][N:22]1[C:23](=[O:24])[C@@H:17]([NH:16][C:15]([C@@H:13]([O:12][C:11](=[O:10])[NH:48][CH2:47][C:46]([F:53])([F:45])[C:49]([F:52])([F:51])[F:50])[CH3:14])=[O:43])[C:18]2[CH:42]=[CH:41][CH:40]=[CH:39][C:19]=2[C:20]2[CH:38]=[CH:37][CH:36]=[CH:35][C:21]1=2)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 58972494Carbonic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester 4-nitro-phenyl ester

Product 1

HCID 58972540(2,2,3,3,3-Pentafluoro-propyl)-carbamic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester

Procedure

Carbonic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester 4-nitro-phenyl ester (65 mg, 0.11 mmol) and 2,2,3,3,3-penta-fluoropropylamine (663 mg, 4.3 mmol) were stirred for 24 h at ambient temperature. After evaporation of all volatile components and chromatography on silica (gradient of heptane/ethyl acetate 0 to 80%), the title compound was obtained as white solid (>98%). MS: m/e=606(M+H+).

Workup

  1. customAfter evaporation of all volatile components and chromatography on silica (gradient of heptane/ethyl acetate 0 to 80%)

Sources & evidence

ORD record
ord-6132c89420d240b7bb7f78716101ff36
Source dataset
uspto-grants-2008_09
Patent number
US07425551B2

Linked notes

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