Water → [4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine

HRID 1271441Notes

Reaction equation

HRID 1271441 reaction equation
C(OC(=O)[N:7]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][CH2:36][CH2:37][N:38]2[CH:42]=[CH:41][N:40]=[N:39]2)=[CH:30][CH:29]=1)[CH2:8][C:9]1[N:10]=[C:11]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([C:24]([F:27])([F:26])[F:25])=[O:23])=[CH:18][CH:17]=2)[O:12][CH:13]=1)(C)(C)C.O.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O.ClCCl>[N:38]1([CH2:37][CH2:36][CH:35]=[CH:34][C:31]2[CH:32]=[CH:33][C:28]([NH:7][CH2:8][C:9]3[N:10]=[C:11]([CH:14]=[CH:15][C:16]4[CH:17]=[CH:18][C:19]([S:22]([C:24]([F:26])([F:27])[F:25])=[O:23])=[CH:20][CH:21]=4)[O:12][CH:13]=3)=[CH:29][CH:30]=2)[CH:42]=[CH:41][N:40]=[N:39]1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 69489717[4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 69486847[4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amineYield 10%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The crude carbamic ester was stirred in a mixture of trifluoroacetic acid/dichloro methane (1:1, 28 ml) for 2 h. Water (50 ml) was added and the solution was neutralized by careful addition of sodium carbonate. The organic layer is separated, washed with water and concentrated. Purification was achieved by flash column chromatography (ethyl acetate/heptane 4:1) and washing with methanol yielding [4-(4-[1,2,3]triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 38 (25 mg, 10%) as a yellow solid.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. concentrationconcentrated
  4. customPurification
  5. washwashing with methanol

Sources & evidence

ORD record
ord-54ace5c1c5844ed39b7f30f2be6d123a
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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