Triethylamine → HCID 86671246, compound

HRID 1952543Notes

Reaction equation

HRID 1952543 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].C(N(CC)CC)C.[C:20]([Si:24]([CH3:37])([CH3:36])[O:25][C:26]1[CH:27]=[C:28]([CH2:32][C:33](O)=[O:34])[CH:29]=[CH:30][CH:31]=1)([CH3:23])([CH3:22])[CH3:21].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(OCC)(=O)C>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:33](=[O:34])[CH2:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([O:25][Si:24]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:36])[CH3:37])[CH:27]=2)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 111923Propylphosphonic anhydrideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 11507264HCID 11507264, compound

Product 1

HCID 86671246HCID 86671246, compoundYield 134.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 2-Amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (1 g, 5.37 mmole), triethylamine (2.9 mL, 20.81 mmol), [3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]acetic acid (0.55 g, 2.065 mmol), 1-propanephosphonic acid cyclic anhydride in 50% ethyl acetate (2.9 mL, 4.871 mmole) in anhydrous THF (50 mL) is heated at 60° C. for 1 h. The reaction was cooled, diluted with water, extracted with Methylene chloride (3×75 mL). The combined organic layers dried over MgSO4, filtered and evaporated. The solid residue was purified by flash column (10-40% EtOAc in hexane to give 2-{2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acetylamino}-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.21 g, 67.4%) as a white solid. MS m/e 435.2 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with Methylene chloride (3×75 mL)
  3. dry with materialThe combined organic layers dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid residue was purified by flash column (10-40% EtOAc in hexane

Sources & evidence

ORD record
ord-f1fac69a8c9b437eac2988dcb5ad4cba
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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