Water → HCID 69105925, compound

HRID 1896706Notes

Reaction equation

HRID 1896706 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:10]=1.[BH4-].[Li+].O>C1COCC1>[C:21]([O:20][C:18](=[O:19])[N:5]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[N:10]=1)[CH2:4][CH2:3][OH:2])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 69105970HCID 69105970, compound

Product 1

HCID 69105925HCID 69105925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 435 mg (1.18 mmol) of (tert-butoxycarbonyl-(4-(4-fluorophenyl)thiazol-2-yl)-amino)acetic acid methyl ester and 51.7 mg (2.37 mmol) of lithium borohydride were stirred in 20 ml of THF at 60° C. for 1 h. After cooling, the mixture was cautiously hydrolyzed with water, the precipitate was filtered off with suction, and water and ethyl acetate were added to the filtrate. The organic phase was separated, washed with water and concentrated. Yield: 273 mg (68%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction, and water and ethyl acetate
  3. additionwere added to the filtrate
  4. customThe organic phase was separated
  5. washwashed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1fc33a5a2c154738894b29bc34dd6a26
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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