Methanol → HCID 69424534, compound

HRID 349859Notes

Reaction equation

HRID 349859 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([OH:22])[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:23])=[O:2])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 69423119HCID 69423119, compound

Product 1

HCID 69424534HCID 69424534, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2S,3R)-3-tert-Butoxycarbonylamino-4-(3-fluoro-phenyl)-2-hydroxy-butyric acid methyl ester (3.28 g, 10.05 mmol, 1 eq), 4N NaOH (4 mL, 16 mmol, 1.6 eq), MeOH (42 mL) and 1,4-dioxane (63 mL) was stirred at ambient temperature for 1.5 h after which the solvents were evaporated. To the residue was added 10% citric acid (100 mL) followed by extraction with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (50 mL), dried (Na2SO4) and concentrated to give the desired product as a cream colored solid (3.06 g, 97%). 1H NMR (DMSO) 7.33–7.26 (m, 1H), 7.02–6.97 (m, 3H), 6.78 (d, J=5.2, 1H), 3.98 (d, J=5.5, 1H), 3.99–3.86 (m, 2H), 2.77–2.82 (m, 2H), 1.27 (s, 9H).

Workup

  1. customwere evaporated
  2. additionTo the residue was added 10% citric acid (100 mL)
  3. extractionfollowed by extraction with EtOAc (100 mL)
  4. washThe organic layer was washed with H2O (100 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a940dfaf23ed43da92e768253d2490d2
Source dataset
uspto-grants-2007_02
Patent number
US07179918B2

Reaction notes

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