O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine → 3alpha-N-(N-tert-butyloxycarbonyl-O-benzyl-L-tyrosyl)aminocholestane

HRID 1595187Notes

Reaction equation

HRID 1595187 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:28][C@@H:29]1[CH2:53][CH2:52][C@@:51]2([CH3:54])[CH:31]([CH2:32][CH2:33][C@@H:34]3[C@@H:50]2[CH2:49][CH2:48][C@@:47]2([CH3:55])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[C@H:39]([CH3:46])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:30]1>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([NH:28][C@@H:29]1[CH2:53][CH2:52][C@@:51]2([CH3:54])[CH:31]([CH2:32][CH2:33][C@@H:34]3[C@@H:50]2[CH2:49][CH2:48][C@@:47]2([CH3:55])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[C@H:39]([CH3:46])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:30]1)=[O:26])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:16]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 108727803Alpha-aminocholestane

Product 1

HCID 540695523alpha-N-(N-tert-butyloxycarbonyl-O-benzyl-L-tyrosyl)aminocholestaneYield 83.5%

Procedure

By using N-tert-butyloxycarbonyl-O-benzyl-L-tyrosine (500 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; 83.5%).

Sources & evidence

ORD record
ord-10da5bd0217f4818a852444fa340f582
Source dataset
uspto-grants-2001_09
Patent number
US06288041B1

Reaction notes

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