Sodium Hydroxide → HCID 56974295, compound

HRID 1759188Notes

Reaction equation

HRID 1759188 reaction equation
C([O:8][C:9](=[O:39])[CH2:10][NH:11][C:12](=[O:38])[C@@H:13]([CH2:34][CH2:35][CH2:36][CH3:37])[NH:14][C:15](=[O:33])[C@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C1C=CC=CC=1.[OH-].[Na+]>CO>[C:21]([O:20][C:18]([NH:17][C@H:16]([C:15]([NH:14][C@@H:13]([C:12]([NH:11][CH2:10][C:9]([OH:39])=[O:8])=[O:38])[CH2:34][CH2:35][CH2:36][CH3:37])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57194949HCID 57194949, compound

Product 1

HCID 56974295HCID 56974295, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.9 g (27.5 mmoles) of the protected tripeptide ester obtained in Step 2 above are dissolved in 300 ml of methanol, 55 ml of a 1 n sodium hydroxide solution are added, and the mixture is allowed to stand at room temperature for 3 hours. Thereafter methanol is distilled off under reduced pressure, the aqueous solution is shaken thrice with 15 ml of ethyl acetate, each, and acidified to pH=3 with solid citric acid. The separated substance is filtered off, washed with water and dried in a vacuum desiccator. 8.1 g (65%) of tert.-butoxycarbonyl-L-tyrosyl-D-norleucyl-glycine are obtained; m.p.: 174°-175° C., Rf2 =0.35-0.45, [α]D20 =+2.0° (c=1%, in dimethyl formamide).

Workup

  1. distillationThereafter methanol is distilled off under reduced pressure
  2. filtrationThe separated substance is filtered off
  3. washwashed with water
  4. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-efa0ec758aa44726aa59ef402103f3de
Source dataset
uspto-grants-1982_07
Patent number
US04339440

Reaction notes

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