1,4-Dioxane → methyl 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoate

HRID 732710Notes

Reaction equation

O1CCOCC1.[C:7]1([C@H:17]([N:19]([CH2:27][C@@H:28]2[C@@H:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:31][NH:30][CH2:29]2)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:48]=[CH:49][C:50]=1[NH:51][C:52](OC1C=CC([N+]([O-])=O)=CC=1)=[O:53])[C:44]([O:46][CH3:47])=[O:45]>C(N(CC)CC)C>[C:22]([O:21][C:20]([N:19]([CH2:27][C@@H:28]1[C@@H:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:31][N:30]([C:52]([NH:51][C:50]2[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][C:41]=2[O:40][CH3:39])=[O:53])[CH2:29]1)[C@@H:17]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:18])=[O:26])([CH3:24])([CH3:25])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A 1,4-dioxane solution of 250 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate was mixed, under ice-cooling, with 0.13 ml of triethylamine and 250 mg of methyl 3-methoxy-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate and stirred overnight at 80° C. The solvent was evaporated under a reduced pressure, and the residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 245 mg of methyl 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoate as a colorless amorphous substance.

Workup

customThe solvent was evaporated under a reduced pressure
customthe residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record: ord-5e5c75f534834dcc819b15adf7e88b60
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585886B2

Reaction notes

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