Hydrochloric Acid → Trt-Cys(Trt)-Cys(Acm)-OH

HRID 1731230Notes

Reaction equation

HRID 1731230 reaction equation
[NH:1]([C:39]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:2]([C:24]([NH:26][C@H:27]([C:35]([O:37]C)=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Na+].Cl>O1CCOCC1>[NH:1]([C:39]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C@H:2]([C:24]([NH:26][C@H:27]([C:35]([OH:37])=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131710552Trt-Cys(Trt)-Cys(Acm)-OMe

Product 1

HCID 131710553Trt-Cys(Trt)-Cys(Acm)-OH

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

5.63 g of Trt-Cys(Trt)-Cys(Acm)-OMe are dissolved in 75 ml of dioxane and 17.5 ml of water and 3.71 ml of 2 N sodium hydroxide solution are cautiously added thereto. After 1 hour at 20°C, the mixture is cooled to 0°C, 3.71 ml of 2 N hydrochloric acid are added and the solution is concentrated under reduced pressure, at room temperature, to approx. 30 ml and is then diluted with 200 ml of chloroform. The solution is washed three times with water and is dried over sodium sulphate. On evaporating off the solvent, the product, which is pure according to thin layer chromatography, is obtained as a white foam.

Workup

  1. concentrationthe solution is concentrated under reduced pressure, at room temperature, to approx. 30 ml
  2. additionis then diluted with 200 ml of chloroform
  3. washThe solution is washed three times with water
  4. dry with materialis dried over sodium sulphate
  5. customOn evaporating off the solvent
  6. customis obtained as a white foam

Sources & evidence

ORD record
ord-f062b32c97c14a0da09007508cfc9836
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

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