Lithium hydroxide, monohydrate → HCID 54348024, compound

HRID 1600847Notes

Reaction equation

HRID 1600847 reaction equation
C[O:2][C:3](=[O:39])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:32])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH:19]([CH3:21])[CH3:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O.[OH-].[Li+]>O1CCOCC1.O>[CH2:12]([O:11][C:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:39])=[O:2])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:32])=[CH:28][CH:29]=1)=[O:22])[CH:19]([CH3:21])[CH3:20])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53776878HCID 53776878, compound

Product 1

HCID 54348024HCID 54348024, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-valyl-4-(phenylcarbonylamino)-L-phenylalanine methyl ester (0.500 g, 0.94 mmol) in dioxane (30 ml) is added lithium hydroxide monohydrate (0.084 g, 2 mmol) in water (10 ml). The reaction is stirred at room temperature overnight. The mixture is taken off in water (20 ml) and washed twice with ethyl acetate (2×20 ml). The aqueous phase is acidified until pH ~2 with 1N hydrochloric acid and extracted three times with ethyl acetate (3×20 ml). The organic layer is dried over anhydrous magnesium sulphate. After filtration and remtial of the solvent invacuo the title compound is obtained as a white solid (0.400 g, 82% yield). MS: [MH]+ =518 [MNH4 ]+ =535.

Workup

  1. washwashed twice with ethyl acetate (2×20 ml)
  2. extractionextracted three times with ethyl acetate (3×20 ml)
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulphate
  4. filtrationAfter filtration and remtial of the solvent invacuo the title compound

Sources & evidence

ORD record
ord-c43f76cdcf26462bb0f024216f08cf71
Source dataset
uspto-grants-1999_11
Patent number
US05977074

Reaction notes

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