Methanol → HCID 69424534, compound

HRID 349861Notes

Reaction equation

HRID 349861 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([O:22]C(=O)CCl)[C@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1.[OH-].[Na+].CO>O1CCOCC1>[C:18]([O:17][C:15]([NH:14][C@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C@H:4]([OH:22])[C:3]([OH:27])=[O:2])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86590377HCID 86590377, compound

Product 1

HCID 69424534HCID 69424534, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2S,3R)-3-tert-butoxycarbonylamino-2-(2-chloro-acetoxy)-4-(3-fluoro-phenyl)-butyric acid methyl ester (4.56 g, 11.3 mmol, 1 eq), 4N NaOH (6.5 mL, 25.9 mmol, 2.3 eq), MeOH (48 mL) and 1.4-dioxane (72 mL) was stirred at ambient temperature for 4 h after which the solvents were removed in vacuo and the residue was charged with H2O (50 mL) and washed with Et2O (100 mL). The aqueous layer was made acidic with 10% citric acid and extracted with EtOAc (2×75 mL). The combined EtOAc layers were washed with H2O (3×50 mL) brine (50 mL), dried (Na2SO4), concentrated, shaken with heptane and filtered to give the desired acid as a white solid (3.3 g, 94%).

Workup

  1. customwere removed in vacuo
  2. additionthe residue was charged with H2O (50 mL)
  3. washwashed with Et2O (100 mL)
  4. extractionextracted with EtOAc (2×75 mL)
  5. washThe combined EtOAc layers were washed with H2O (3×50 mL) brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. stirringshaken with heptane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2e0461dc62914ae888c029078ad4f01c
Source dataset
uspto-grants-2007_02
Patent number
US07179918B2

Reaction notes

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