Ammonium Acetate → HCID 178433035, compound

HRID 549352Notes

Reaction equation

HRID 549352 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]=[C:18]([CH3:28])[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:15])[CH:10]([CH2:29][C:30](OCC(C2C=CC(F)=CC=2)=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:43]([O-])(=O)[CH3:44].[NH4+:47]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]=[C:18]([CH3:28])[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:15])[CH:10]([CH2:29][C:30]2[NH:47][CH:10]=[C:9]([C:43]3[CH:44]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:8]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 67158091(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178433035HCID 178433035, compound

Procedure

(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester from description 111 (0.360 g) and anhydrous ammonium acetate were heated to 140° C. under argon for 1.5 hours with stirring. After cooling, the reaction mixture was partitioned between dichloromethane and saturated potassium carbonate solution. The organic solution was washed with brine, dried (MgSO4) and evaporated. The residue was chromatographed over silica gel, eluting with 0 to 10% ethanol in ethyl acetate. The title compound was obtained as a white foam (0.125 g), mass spectrum (API+) 580 [MH+], C30H31F2N5O3S requires 579.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between dichloromethane and saturated potassium carbonate solution
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed over silica gel
  7. washeluting with 0 to 10% ethanol in ethyl acetate

Sources & evidence

ORD record
ord-2e6c52e290054983b1fe7e6833fab496
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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