N-(tert-butoxycarbonyl)glycine → 3alpha-N-(N-tert-butyloxycarbonylglycyl)amino-cholestane

HRID 1595192Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:13][C@@H:14]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[CH:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:40])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:15]1>>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:13][C@@H:14]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[CH:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:40])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:15]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycine

HCID 108727803Alpha-aminocholestane

Product 1

HCID 545015063alpha-N-(N-tert-butyloxycarbonylglycyl)amino-cholestane

Procedure

By using tert-butyloxycarbonylglycine (522 mg, 2.98 mmol) and 3α-aminocholestane (1.16 g, 2.99 mmol), the title compound was obtained in the same manner as in Synthetic Example BB1 (1.65 g, quantitative).

Sources & evidence

ORD record: ord-cff281e97c2b4fa19337943b60331b4f
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288041B1

Reaction notes

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