(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid → 3alpha-N-(N-tert-butyloxycarbonyl-O-benzyl-D-seryl)aminocholestane

HRID 1595188Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C@@H:23]1[CH2:47][CH2:46][C@@:45]2([CH3:48])[CH:25]([CH2:26][CH2:27][C@@H:28]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:49])[C@H:29]3[CH2:30][CH2:31][C@@H:32]2[C@H:33]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:24]1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:19]([NH:22][C@@H:23]1[CH2:47][CH2:46][C@@:45]2([CH3:48])[CH:25]([CH2:26][CH2:27][C@@H:28]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:49])[C@H:29]3[CH2:30][CH2:31][C@@H:32]2[C@H:33]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:24]1)=[O:21])[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HCID 108727803Alpha-aminocholestane

Product 1

HCID 542825053alpha-N-(N-tert-butyloxycarbonyl-O-benzyl-D-seryl)aminocholestaneYield 83%

Procedure

By using N-tert-butyloxycarbonyl-O-benzyl-D-serine (600 mg, 2.03 mmol) and 3α-aminocholestane (866 mg, 2.23 mmol), the title compound was obtained in the same manner as in Synthetic Example BB1 (1.13 g, yield; 83%).

Sources & evidence

ORD record: ord-8a1cbf2faeeb467ba2cd879e64043617
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288041B1

Reaction notes

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