Methanol → HCID 15755327, compound

HRID 2082235Notes

Reaction equation

HRID 2082235 reaction equation
[NH:1]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:2]([C:8]([NH:10][C@@H:11]([C:24]([NH:26][C@H:27]([C:35]([O:37]CC1C=CC=CC=1)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15](C=O)[CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[OH-].[Na+].CO.O>C1COCC1>[NH:1]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:2]([C:8]([NH:10][C@@H:11]([C:24]([NH:26][C@H:27]([C:35]([OH:37])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 14798Sodium HydroxideHCID 130847N(alpha)-(N(alpha)-(N(alpha)-(tert-butyloxycarbonyl)glutaminyl)-N(1)-formyl-tryptophyl)phenylalanine benzyl ester

Product 1

HCID 15755327HCID 15755327, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Boc-Gln-D-Trp(CHO)-Phe-OBzl (1.2 g) and 1N sodium hydroxide (3.6 ml) in a mixture of THF (30 ml), methanol (10 ml) and water (5 ml) was stirred for 1.5 hours. After adding water (10 ml), the organic solvent was evaporated. The resulting aqueous solution was washed with diethyl ether, acidified with 10% citric acid solution and allowed to stand in a refrigerator overnight. The precipitates were filtered, washed with water and recrystallized with a mixture of ethanol and water to give Boc-Gln-D-Trp-Phe-OH (0.80 g).

Workup

  1. customthe organic solvent was evaporated
  2. washThe resulting aqueous solution was washed with diethyl ether
  3. customto stand in a refrigerator overnight
  4. filtrationThe precipitates were filtered
  5. washwashed with water
  6. customrecrystallized with a mixture of ethanol and water

Sources & evidence

ORD record
ord-9d796689b9a14390a5f49684e68e4e6d
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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