Water → N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycine

HRID 1680574Notes

Reaction equation

HRID 1680574 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@@H:21]([C:26]([NH:28][CH2:29][C:30]([O:32]C)=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.[OH-].[K+]>CO>[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@@H:21]([C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13216983Boc-Tyr-D-Met-Gly-OMe

Product 1

HCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.02 Grams of methyl Boc-L-tyrosyl-D-methionyl-glycinate is dissolved in 30 ml of methyl alcohol and water is added until the solution becomes cloudy. A 4 M solution of potassium hydroxide is added to maintain the pH at 12-13. When the pH is stable at 13 for 30 minutes, the methanol is removed under reduced pressure. The aqueous solution is filtered and adjusted to pH 3 with concentrated hydrochloric acid. The product crystallizes and is removed by filtration and washed with water to give Boc-L-tyrosyl-D-methionyl-glycine which is represented by the following formula

Workup

  1. temperatureto maintain the pH at 12-13
  2. customthe methanol is removed under reduced pressure
  3. filtrationThe aqueous solution is filtered
  4. customThe product crystallizes
  5. customis removed by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-64eb7f3d56264207be990173c5a90fbc
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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