N2-((tert-Butoxy)carbonyl)-L-asparagine → 3alpha-N-(N-tert-butyloxycarbonyl-L-asparagyl)aminocholestane

HRID 1595191Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][C:11](=[O:13])[NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C@@H:18]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[CH:20]([CH2:21][CH2:22][C@@H:23]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:44])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:19]1>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([NH:17][C@@H:18]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[CH:20]([CH2:21][CH2:22][C@@H:23]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:44])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:19]1)=[O:16])[CH2:10][C:11](=[O:13])[NH2:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

HCID 108727803Alpha-aminocholestane

Product 1

HCID 206837353alpha-N-(N-tert-butyloxycarbonyl-L-asparagyl)aminocholestaneYield 56%

Procedure

By using N-tert-butyloxycarbonyl-L-asparagine (464 mg, 2.00 mmol) and 3α-aminocholestane (777 mg, 2.00 mmol), the title compound was obtained in the same manner as in Synthetic Example BB1 (670 mg, yield; 56%).

Sources & evidence

ORD record: ord-aa6986cf6a6e4b12b974ebeaa81a42a8
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288041B1

Reaction notes

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