Acetone → HCID 86738863, compound

HRID 544121Notes

Reaction equation

HRID 544121 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 1N sodium hydroxide, 1N hydrochloric acid, brine, dried over sulfate and evaporated to afford bis N-acetyl-D-cystine bis allyl ester. Treatment of this bis compound according to the procedure of Preparation I affords the title compound.

Workup

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

Sources & evidence

ORD record
ord-63b7f7d0719a4dd3a7fa4a3113802acb
Source dataset
uspto-grants-1984_05
Patent number
US04448782

Reaction notes

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