Lithium Hydroxide → HCID 86718362, compound

HRID 1518755Notes

Reaction equation

HRID 1518755 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH:5]([CH2:9][O:10][CH3:11])[CH2:6][O:7][CH3:8].[Li+].[OH-]>C1COCC1.CO.O>[CH2:16]([O:15][C:13]([NH:12][C@@H:4]([CH:5]([CH2:9][O:10][CH3:11])[CH2:6][O:7][CH3:8])[C:3]([OH:23])=[O:2])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68065838HCID 68065838, compound

Product 1

HCID 86718362HCID 86718362, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-Benzyloxycarbonylamino-4-methoxy-3-methoxymethyl-butyric acid methyl ester (100 mg, 0.30 mmol, 1.0 equiv) in THF/MeOH/water (0.5 mL/0.5 mL/0.5 mL) was added LiOH*H2O (38.7 mg, 0.92 mmol, 3.0 equiv). After stirring at 0° C. for 1 hour, the reaction was quenched by addition of 1.0 N aq. HCl solution until the pH of the solution was approximately 4. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. MS m/z (M+1) 312.2

Workup

  1. customthe reaction was quenched by addition of 1.0 N aq. HCl solution until the pH of the solution
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b52985c0c8234d218d8b294fcf653b90
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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