Triethylamine → HCID 57513828, compound

HRID 2368414Notes

Reaction equation

HRID 2368414 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:17])[C:13]([NH2:16])([CH3:15])[CH3:14])=[N:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:17])[C:13]([NH:16][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([F:31])=[CH:33][CH:34]=2)([CH3:15])[CH3:14])=[N:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 57513827HCID 57513827, compound

Product 1

HCID 57513828HCID 57513828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2-Amino-2-methyl-propionylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (249 mg, 0.748 mmol), triethylamine (300 uL. 2.16 mmol) and 4-fluorobenzoyl chloride (135 uL, 1.13 mmol) in dichloromethane (3 mL) was stirred at RT for 2 h and partitioned between ethyl acetate and aq. K2CO3. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 456.1 (MH+).

Workup

  1. custompartitioned between ethyl acetate and aq. K2CO3
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-e418e6202ff4428aa86afcc0f2d91e81
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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