Lithium hydroxide, monohydrate → HCID 12799294, compound

HRID 1680584Notes

Reaction equation

HRID 1680584 reaction equation
[C:1]([NH:8][CH:9]([C:20]([NH:22][C@@H:23]([C:28]([O:30]C)=[O:29])[CH2:24][CH2:25][S:26][CH3:27])=[O:21])[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.[OH-].[Li+].S(=O)(=O)(O)[O-].[K+]>CO.O>[C:1]([NH:8][CH:9]([C:20]([NH:22][C@@H:23]([C:28]([OH:30])=[O:29])[CH2:24][CH2:25][S:26][CH3:27])=[O:21])[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 53707215HCID 53707215, compound

Product 1

HCID 12799294HCID 12799294, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.27 g of methyl Boc-2,6-dimethyl-DL-tyrosyl-D-methioninate in 14 ml of methanol is added a solution of 1.18 g of lithium hydroxide hydrate in 14 ml of water. The reaction mixture is stirred for 3 hours in the cold then 100 ml of a 5% solution of potassium bisulfate is added to bring the pH to 2.5 The gummy product which forms is extracted with ethyl acetate. The ethyl acetate layers are collected and combined, then washed with water and dried over magnesium sulfate. The solution is filtered to remove the magnesium sulfate and the solvent is removed under reduced pressure to give Boc-2,6-dimethyl-DL-tyrosyl-D-methionine.

Workup

  1. additionis added
  2. extractionforms is extracted with ethyl acetate
  3. customThe ethyl acetate layers are collected
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution is filtered
  7. customto remove the magnesium sulfate
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-30e6e16bc7bc440f9da3f66a0b357ae1
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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