Sodium borohydride → HCID 66207352, compound

HRID 661118Notes

Reaction equation

HRID 661118 reaction equation
Cl.[NH2:2][CH:3]([C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].BrC1SC(Br)=C(Cl)N=1.[BH4-].[Na+]>CO>[NH2:2][CH:3]([CH:9]([OH:20])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 123331592,5-Dibromo-4-chloro-1,3-thiazoleHCID 68993625HCID 68993625, compound

Product 1

HCID 66207352HCID 66207352, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-amino-3-oxo-3-(4-(trifluoromethyl)phenyl)propanoate hydrochloride (20.00 g, 64.17 mmol), was prepared as described by Singh, J., Tetrahedron Letters 34 (2), 211-214 (1993), was charged into a 500 mL round-bottomed flask and mixed with MeOH (160 mL). Sodium borohydride (3.641 g, 96.25 mmol) was added to the above mixture slowly at 0° C. The cooling bath was removed after the addition. The mixture was stirred at room temperature for 2 hours, and then filtered through a silica gel column in a funnel. The silica gel was washed with 10% MeOH (2.0M NH3)—CH2Cl2. The filtrate was concentrated in vacuo, and the crude product was triturated with 25% EtOAc-Hexane to provide the pure product as a white solid. LCMS (API-ES) m/z (%): 278 (M++H).

Workup

  1. customThe cooling bath was removed
  2. additionafter the addition
  3. filtrationfiltered through a silica gel column in a funnel
  4. washThe silica gel was washed with 10% MeOH (2.0M NH3)—CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude product was triturated with 25% EtOAc-Hexane

Sources & evidence

ORD record
ord-04b0cef440db464a99dc24dc7a503d6c
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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