tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate → 1-[2(S)-hydroxy-3(S)-(tert-butoxycarbonylamino)-4-phenylbutyl]-1-[4-biphenylylmethyl]-2-[tert-butoxycarbonyl)hydrazine

HRID 1291778Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][C:28]([NH:30][C@H:31]([C@H:39]1[O:41][CH2:40]1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>CO.O>[OH:41][C@H:39]([C@@H:31]([NH:30][C:28]([O:27][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:29])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:40][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 58.7 g (197 mmol) of N1 -(tert-butoxycarbonyl)-N2 -(4-biphenylylmethyl)hydrazine and 51.8 g (197 mmol) of N-(tert-butoxycarbonyl)-2(S)-amino-1-phenyl-3(R)-3,4-epoxybutane (=(2R,3S)-1-[3-Boc-amino-2-phenylethyl]-oxirane) in 700 ml of absolute methanol is heated to reflux temperature during 16 h. The mixture is then cooled to 0° C. and diluted with 1.5 l of water. The solid is filtered and dried at 70° C. for 6 h to give the title compound:

Workup

temperatureto reflux temperature during 16 h
filtrationThe solid is filtered
customdried at 70° C. for 6 h

Sources & evidence

ORD record: ord-58b67172884f42978c532a1d2cf3ff50
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753652

Reaction notes

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