Acetone → HCID 86738863, compound

HRID 851160Notes

Reaction equation

HRID 851160 reaction equation
[C:1]([NH:4][C@@H:5]([C:18]([OH:20])=[O:19])[CH2:6][S:7][S:8][CH2:9][C@@H:10]([NH:14][C:15](=[O:17])[CH3:16])[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH2:28](Br)[CH:29]=[CH2:30].[CH3:32][C:33]([CH3:35])=O>O>[CH2:28]([O:12][C:11](=[O:13])[C@H:10]([NH:14][C:15](=[O:17])[CH3:16])[CH2:9][S:8][S:7][CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:18]([O:20][CH2:35][CH:33]=[CH2:32])=[O:19])[CH:29]=[CH2:30]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 8471TriethylamineHCID 11461484HCID 11461484, compound

Product 1

HCID 86738863HCID 86738863, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of bis-N-acetyl D-cystine (3.2 g) in acetone (30 ml) containing triethylamine (4.0 g) is stirred with allyl bromide (4 ml) for 24 hours. The mixture is diluted with water, washed with 1 N sodium hydroxide, 1 N hydrochloric acid, brine, dried over sulfate and evaporated to afford bis N-acetyl-D-cystine bis allyl ester. Treatment of this bis compound accoding to the procedure of Preparation I affords the title compound.

Workup

  1. washwashed with 1 N sodium hydroxide, 1 N hydrochloric acid, brine
  2. dry with materialdried over sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-3b1a3eb78aaa4226919489f9731d5420
Source dataset
uspto-grants-1983_05
Patent number
US04382949

Reaction notes

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