2,2,3,3,3-Pentafluoropropylamine → HCID 11226666, compound

HRID 1374575Notes

Reaction equation

HRID 1374575 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[C@@H:3]1[NH:22][C:23]([C@@H:25]([O:27][C:28](=O)[O:29]C1C=CC([N+]([O-])=O)=CC=1)[CH3:26])=[O:24].[F:40][C:41]([F:48])([C:44]([F:47])([F:46])[F:45])[CH2:42][NH2:43]>ClCCl.C(OC(=O)C)C>[O:1]=[C:2]1[N:8]([CH2:9][C:10]([F:12])([F:13])[F:11])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[C@@H:3]1[NH:22][C:23]([C@@H:25]([O:27][C:28](=[O:29])[NH:43][CH2:42][C:41]([F:48])([F:40])[C:44]([F:47])([F:46])[F:45])[CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 131726206HCID 131726206, compound

Product 1

HCID 11226666HCID 11226666, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

0.065 g (0.12 mmol) carbonic acid 4-nitro-phenyl ester (S)-1-[(S)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester and 0.26 ml 2,2,3,3,3. pentafluoropropylamine were stirred at room temperature over night. Chromatography on silicagel with dichloromethane/ethylacetate (100-40/0-60) yielded 0.06 g (86%) (2,2,3,3,3-Pentafluoro-propyl)-carbamic acid (S)-1-[(S)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester as white foam, MS: m/e: 554.3 (M+H+), [α] 589=−4.40° (0.75% in CHCl3).

Sources & evidence

ORD record
ord-8e2fe2b5371a4fa0b55cbbaa60cf5e9f
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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