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

HRID 1374573Notes

Reaction equation

HRID 1374573 reaction equation
[N+](C1C=CC([O:10][C:11](=O)[O:12][C@H:13]([C:15](=[O:37])[NH:16][C@@H:17]2[C:23](=[O:24])[N:22]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:21]3[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=3[C:19]3[CH:33]=[CH:34][CH:35]=[CH:36][C:18]2=3)[CH3:14])=CC=1)([O-])=O.[F:39][C:40]([F:47])([C:43]([F:46])([F:45])[F:44])[CH2:41][NH2:42]>ClCCl.C(OC(=O)C)C>[CH:26]1([CH2:25][N:22]2[C:23](=[O:24])[C@@H:17]([NH:16][C:15]([C@@H:13]([O:12][C:11](=[O:10])[NH:42][CH2:41][C:40]([F:47])([F:39])[C:43]([F:46])([F:45])[F:44])[CH3:14])=[O:37])[C:18]3[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=3[C:20]3[CH:32]=[CH:31][CH:30]=[CH:29][C:21]2=3)[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 86597454carbonic acid (S)-1-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester 4-nitro-phenyl ester

Product 1

HCID 11307013(2,2,3,3,3-Pentafluoro-propyl)-carbamic acid (s)-1-((s)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5h-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

0.61 g (1.18 mmol) 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 and 2.5 ml 2,2,3,3,3. pentafluoropropylamine were stirred at room temperature over night. Chromatography on silicagel with dichloromethane/ethylacetate (100-70/0-30) yielded 0.61 g (98%) (2,2,3,3,3-pentafluoro-propyl)-carbamic acid (S)-1-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-ethyl ester as white solid; MS: m/e: 526.0 (M+H+), [α] 589=−940° (1.1% in MeOH).

Sources & evidence

ORD record
ord-7a4836a0a4e54ab595141ac42af663b2
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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