Lithium hydroxide, monohydrate → EtOCO-D,L-Phe(alphaMe)-Pro-OH

HRID 375096Notes

Reaction equation

HRID 375096 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]([CH3:32])([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].O[Li].O>O1CCOCC1.O>[CH2:1]([O:3][C:4]([NH:6][C:7]([CH3:32])([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131719051EtOCO-D,L-Phe(alphaMe)-Pro-OBzl

Product 1

HCID 131719052EtOCO-D,L-Phe(alphaMe)-Pro-OHYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of EtOCO-D,L-Phe(αMe)-Pro-OBzl (13.2 g, 30 mmol) in p-dioxane (250 mL) was added a solution of LiOH·H2O (6.3 g, 151 mmol) in water (125 mL). After stirring for 2.5 h, the solvent was removed in vacuo and the residue was diluted with water and washed three times with diethyl ether. The aqueous phase was then taken to pH 2 with conc. HCl and extracted three times with ethyl acetate. The combined ethyl acetate extracts were dried (Na2SO4), filtered and concentrated in vacuo to give 10.7 g of a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. washwashed three times with diethyl ether
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d446c90f940d4f898946d1a813d92e9e
Source dataset
uspto-grants-1996_01
Patent number
US05484772

Reaction notes

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