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

HRID 1374570Notes

Reaction equation

HRID 1374570 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C@@H:3]1[NH:17][C:18]([C@@H:20]([O:22][C:23](=O)[O:24]C1C=CC([N+]([O-])=O)=CC=1)[CH3:21])=[O:19].[F:35][C:36]([F:43])([C:39]([F:42])([F:41])[F:40])[CH2:37][NH2:38]>ClCCl.C(OC(=O)C)C>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C@@H:3]1[NH:17][C:18]([C@@H:20]([O:22][C:23](=[O:24])[NH:38][CH2:37][C:36]([F:43])([F:35])[C:39]([F:42])([F:41])[F:40])[CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 86597453carbonic acid 4-nitro-phenyl ester (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester

Product 1

HCID 11476951(2,2,3,3,3-Pentafluoro-propyl)-carbamic acid (s)-1-((s)-6-oxo-6,7-dihydro-5h-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

0.12 g (0.25 mmol) carbonic acid 4-nitro-phenyl ester (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester and 543 μl 2,2,3,3,3. pentafluoropropylamine were stirred at room temperature over night. Chromatography on silicagel with dichloromethane/ethylacetate (100-0 to 75-25) yielded 0.075 g (63%) (2,2,3,3,3-pentafluoro-propyl)-carbamic acid (S)-1-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester as white solid. MS: m/e: 472.1 (M+H+), [α] 589=−76.4° (1% in MeOH).

Sources & evidence

ORD record
ord-0f18cdb3def845f7831b889dff5d1c3c
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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