Hydrochloric Acid → HCID 88118295, compound

HRID 1018681Notes

Reaction equation

HRID 1018681 reaction equation
C[O:2][C:3](=[O:29])[C@@H:4]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1.O.[OH-].[Li+].Cl>CO.O>[C:25]([O:24][C:22]([NH:21][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:8]([P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1)[C:3]([OH:2])=[O:29])=[O:23])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54474618HCID 54474618, compound

Product 1

HCID 88118295HCID 88118295, compoundYield 152.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a cooled (0° C.) solution (S)-2-tert-butoxycarbonylamino-3-[3-(diethoxy-phosphoryl)-4-hydroxy-phenyl]-propionic acid methyl ester (423 mg, 0.98 mmol) in MeOH (4 mL) was added lithium hydroxide monohydrate (84 mg, 2.0 mmol) in H2O (4 mL). After 1 h, the reaction was allowed to warm to rt. After 2.5 h, the solution was carefully acidified to pH 2 using 0.5 N HCl and extracted twice with EtOAc. The organic extracts were pooled, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 379 mg (91%) of a yellow foam. The crude material was carried on without further purification. Electrospray Mass Spectrum (50/50 acetonitrile/water) m/z 416 (M−H).

Workup

  1. waitAfter 2.5 h
  2. extractionextracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66ac36ae2d2d44dc9dfc37cac09a6991
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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