Boc-Lys(Z)-OH → 3alpha-N-(Nalpha-tert-butyloxycarbonyl-Nepsilon-benzyloxycarbonyl-L-lysyl)aminocholestane

HRID 1595190Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=O)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[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:27])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 2724765Boc-Lys(Z)-OH

HCID 108727803Alpha-aminocholestane

Product 1

HCID 702514993alpha-N-(Nalpha-tert-butyloxycarbonyl-Nepsilon-benzyloxycarbonyl-L-lysyl)aminocholestane

Procedure

By using Nα-tert-butyloxycarbonyl-Nε-benzyloxycarbonyl-L-lysine (760 mg, 2.00 mmol) and 3α-aminocholestane (853 mg, 2.20 mmol), the title compound was obtained in the same manner as in Synthetic Example BB 1 (1.57 g, quantitative).

Sources & evidence

ORD record: ord-8c77b2e8750a46b58564cf6f1e9fc9a8
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288041B1

Reaction notes

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