Dicyclohexylcarbodiimide → succinimidyl N-(cholest5-en-3beta-oxycarbonyl)glycinate

HRID 622725Notes

Reaction equation

HRID 622725 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].O[N:37]1[C:41](=[O:42])[CH2:40][CH2:39][C:38]1=[O:43].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1.C(Cl)(Cl)Cl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33]([O:35][N:37]4[C:41](=[O:42])[CH2:40][CH2:39][C:38]4=[O:43])=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 14168269N-(cholest-5-en-3beta-oxycarbonyl)glycine

Product 1

HCID 14168272succinimidyl N-(cholest5-en-3beta-oxycarbonyl)glycinateYield 92.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(cholest-5-en-3β-oxycarbonyl)glycine (2.92 g) in a mixture of dioxane (40 ml) and chloroform (6 ml) were added successively N-hydroxysuccinimide (0.69 g) and dicyclohexylcarbodiimide (1.236 g) at 0° C. and the reaction mixture was stood for 16 hours in a refrigerator. The resulting precipitate was collected by filtration and the filtrate was concentrated in vacuo to give succinimidyl N-(cholest5-en-3β-oxycarbonyl)glycinate (3.23 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-59d6bf476f944748950b28a6ee156ce1
Source dataset
uspto-grants-1988_09
Patent number
US04772594

Reaction notes

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