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

HRID 1648379Notes

Reaction equation

HRID 1648379 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-8ef384a9d718467295dd6a07f794ca84
Source dataset
uspto-grants-1995_07
Patent number
US05436229

Reaction notes

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