Sodium Hydroxide → HCID 131717774, compound

HRID 2082231Notes

Reaction equation

HRID 2082231 reaction equation
[NH:1]([C:48]([CH3:50])=[O:49])[C@H:2]([C:6]([NH:8][C@@H:9]([C:26]([NH:28][C@H:29]([C:37]([N:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH3:40])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][C:21]([O:23]CC)=[O:22])[CH:12]=1)=[O:7])[C@@H:3]([CH3:5])[OH:4].[OH-].[Na+]>C(O)C>[NH:1]([C:48]([CH3:50])=[O:49])[C@H:2]([C:6]([NH:8][C@@H:9]([C:26]([NH:28][C@H:29]([C:37]([N:39]([CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH3:40])=[O:38])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:27])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][C:21]([OH:23])=[O:22])[CH:12]=1)=[O:7])[C@@H:3]([CH3:5])[OH:4]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 131717775HCID 131717775, compound

Product 1

HCID 131717774HCID 131717774, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ac-Thr-D-Trp(CH2CO2Et)-Phe-NMeBzl (0.98 g) in ethanol (25 ml) was added 0.1N sodium hydroxide solution (14.3 ml) under ice-cooling. After stirring two hours, 0.1N sodium hydroxide solution (2.0 ml) was added and the mixture was stirred for additional two hours. The ethanol was evaporated and the solution was extracted twice with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid and extracted twice with ethyl acetate. The extract was washed with sodium chloride solution and concentrated to give Ac-Thr-D-Trp(CH2CO2H)-Phe-NMeBzl as an amorphous solid (0.90 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for additional two hours
  3. customThe ethanol was evaporated
  4. extractionthe solution was extracted twice with ethyl acetate
  5. extractionextracted twice with ethyl acetate
  6. washThe extract was washed with sodium chloride solution
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79864d2c5bd04ab68c59160c4136ff7e
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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