Trifluoroacetic acid → Trifluoroacetic acid

HRID 408494Notes

Reaction equation

HRID 408494 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH:13](O)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][N:12]=1)(C)(C)C.C([SiH](CC)CC)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>ClCCl>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][C:10]1[S:9][C:8]([NH2:7])=[N:12][CH:11]=1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58609916{5-[1-Hydroxy-2-(2-methoxy-phenyl)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidYield 42%HCID 867128295-[2-(2-Methoxy-phenyl)-ethyl]-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {5-[1-Hydroxy-2-(2-methoxy-phenyl)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (28 g, 0.080 mol), triethylsilane (130 g, 1.12 mol) and trifluoroacetic acid (250 g, 2.24 mol) in dichloromethane (500 mL) was stirred at room temperature for 15 hours. The mixture was evaporated to dryness and then stirred in water. The solid was filtered and washed with ether to give 5-[2-(2-Methoxy-phenyl)-ethyl]-thiazol-2-ylamine as a trifluoracetic acid salt (11 g, 0.033 mol, yield 42%). ESI-MS m/z cacl. 234.08. found 235.16 (M+1)+ 1H NMR (CDCl3) δ 8.81 (br, 2H), 7.20 (t, 1H), 7.12 (d, 1H), 6.95 (m, 2H), 6.85 (t, 1H), 3.76 (s, 3H), 2.83 (d, 2H), 2.80 (d, 2H).

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringstirred in water
  3. filtrationThe solid was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-2e5b832b264c43ff8e8bfb454de3c6a7
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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