Hydrochloric Acid → HCID 11225270, compound

HRID 1166451Notes

Reaction equation

HRID 1166451 reaction equation
[N:1]1([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:25][CH2:24][CH2:23][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([N:14]1[CH2:22][CH2:21][CH2:20][C@H:15]1[C:16]([O:18]C)=[O:17])=[O:13])=[O:9])[CH3:7])=[O:4].[OH-].[Na+].Cl>CO>[N:1]1([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:25][CH2:24][CH2:23][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([N:14]1[CH2:22][CH2:21][CH2:20][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:9])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131724052HCID 131724052, compound

Product 1

HCID 11225270HCID 11225270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude oil of the N-Cbz-Pro-Ala-Gly-Pro-OCH3 (5g, 12 mmol) was dissolved in methanol (20 ml) in a round bottom flask. The flask was placed in an ambient temperature water bath. 1 N Sodium hydroxide solution (12 ml) was added cautiously. The solution was stirred for 3.5 hours after which time 1 N HCl solution (12 ml) was added. The solution was concentrated on the roto-evaporator and a few more drops of 1 N HCl was added until the pH is approximately 1.5 with pH paper. The water was removed with the vacuum pump to give an oil, which was recrystalized slowly from ethanol.

Workup

  1. customwas placed in an ambient temperature
  2. additionwas added
  3. concentrationThe solution was concentrated on the roto-evaporator
  4. additiona few more drops of 1 N HCl was added until the pH is approximately 1.5 with pH paper
  5. customThe water was removed with the vacuum pump
  6. customto give an oil, which
  7. customwas recrystalized slowly from ethanol

Sources & evidence

ORD record
ord-df0ab96ccb99495d85b2d4ae5cde2c8f
Source dataset
uspto-grants-2003_09
Patent number
US06613879B1

Reaction notes

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