Trifluoroacetic acid → 2-Amino-5-(2-methoxy-benzyl)-thiazole-4-carboxylic acid ethyl ester

HRID 408499Notes

Reaction equation

HRID 408499 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:21]C(OC(C)(C)C)=O)[S:9][C:10]=1[CH:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[O:5])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:21])[S:9][C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 586098972-tert-Butoxycarbonylamino-5-[hydroxy-(2-methoxy-phenyl)-methyl]-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 574569472-Amino-5-(2-methoxy-benzyl)-thiazole-4-carboxylic acid ethyl esterYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-tert-butoxycarbonylamino-5-[hydroxy-(2-methoxy-phenyl)-methyl]-thiazole-4-carboxylic acid ethyl ester (12 g, 29 mmol), triethylsilane (52 g, 45 mmol), and trifluoroacetic acid (100. g, 89.6 mmol) was stirred for 15 hours in dichloromethane (150 mL). The mixture was evaporated to dryness and then diluted with water. The precipitated solid was filtered and washed with water, diethyl ether, and petroleum ether to give the pure target molecule as a trifluoroacetic acid salt (7.6 g, 19 mmol, 64%). ESI-MS m/z calc. 292.09. found; 292.25 (M+1)+ 1H NMR (CDCl3) δ 7.7 (br, 2H), 7.24 (t, 1H), 7.17 (d, 1H), 6.99 (d, 1H), 6.88 (t, 1H), 4.22-4.25 (m, 4H), 3.78 (s, 3H), 1.26 (t, 3H).

Workup

  1. customThe mixture was evaporated to dryness
  2. additiondiluted with water
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water, diethyl ether, and petroleum ether

Sources & evidence

ORD record
ord-cd8dfd0ed8da4a4696df656d1a66c19f
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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