Sodium Hydroxide → HCID 12888631, compound

HRID 126791Notes

Reaction equation

HRID 126791 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([O:37]C)=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH-].[Na+]>CO.CCOC(C)=O>[NH:1]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([OH:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12888623HCID 12888623, compound

Product 1

HCID 12888631HCID 12888631, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2.0 g of Boc-Tyr-DAla-Phe-Met-OCH3 (prepared as in Step C of Example 1A) in 50 ml of methanol was added 8.0 ml of 1 N NaOH. Evaporation of the solution after stirring at room temperature for 1 hour gave a residue which was dissolved in 30 ml of EtOAc and washed with 1 N HCl (4×50 ml) and saturated NaCl (3×50 ml). The MgSO4 dried EtOAc solution was evaporated to a residue which was purified by chromatography on silica gel with a gradient of chloroform to 10% acetic acid in chloroform to give 1.12 g (57%) of Boc-Tyr-DAla-Phe-Met-OH, m.p. 135° C.

Workup

  1. customEvaporation of the solution
  2. customgave a residue which
  3. washwashed with 1 N HCl (4×50 ml) and saturated NaCl (3×50 ml)
  4. customThe MgSO4 dried EtOAc solution was evaporated to a residue which
  5. customwas purified by chromatography on silica gel with a gradient of chloroform to 10% acetic acid in chloroform

Sources & evidence

ORD record
ord-0b3d91677cc2489583e7468521d0afc9
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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