Methanol → HCID 131722497, compound

HRID 324258Notes

Reaction equation

HRID 324258 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:2]([C:12]([NH:14][C@H:15]([C:23]([NH:25][C@H:26]([C:30]([NH:32][CH:33](OC)[C:34]([OH:36])=[O:35])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].CO>O1CCOCC1>[NH:1]([C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[C@H:2]([C:12]([NH:14][C@H:15]([C:23]([NH:25][C@H:26]([C:30]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 131722498HCID 131722498, compound

Product 1

HCID 131722497HCID 131722497, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Mix Boc-Ser(OBn)-Phe-Val-Gly(OMe), SEQ ID NO:23, (3.95 g, 6.45 mmol), 1 N sodium hydroxide (39 mL, 39 mmol), methanol (100 mL) and dioxane (60 mL). Stir at room temperature under a nitrogen atmosphere until hydrolysis is complete. Evaporate the solvent in vacuo and purify by silica gel chromatography (chloroform) to give Boc-Ser(OBn)-Phe-Val-Gly, SEQ ID NO:25, (3.32 g, 85.4%).

Workup

  1. customEvaporate the solvent in vacuo
  2. custompurify by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-1e5987a64196496bbe7c157758e1483c
Source dataset
uspto-grants-2001_04
Patent number
US06218364B1

Reaction notes

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