Trifluoroacetic acid → HCID 11677427, compound

HRID 494315Notes

Reaction equation

HRID 494315 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:18][O:19][CH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][C@H:23]([CH2:27][O:28][C:29]([CH3:38])([CH3:37])[C:30]([O:32]C(C)(C)C)=[O:31])[CH2:22]1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:15])[F:17])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:18][O:19][CH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][C@H:23]([CH2:27][O:28][C:29]([CH3:37])([CH3:38])[C:30]([OH:32])=[O:31])[CH2:22]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57682953HCID 57682953, compound

Product 1

HCID 11677427HCID 11677427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

270 mg of tert-butyl 2-{(1S,3R)-3-[5-ethyl-2-(4-trifluoromethylphenyl)oxazol-4-ylmethoxymethyl]cyclohexylmethoxy}-2-methylpropionate are dissolved in 5 ml of dichloromethane and 2.5 ml of trifluoroacetic acid and stirred overnight. The solution is then completely evaporated, and the residue is purified by preparative HPLC, resulting in 127 mg of 2-{(1S,3R)-3-[5-ethyl-2-(4-trifluoromethylphenyl)oxazol-4-ylmethoxymethyl]cyclohexylmethoxy}-2-methylpropionic acid as yellow oil.

Workup

  1. customThe solution is then completely evaporated
  2. customthe residue is purified by preparative HPLC
  3. customresulting in 127 mg of 2-{(1S,3R)-3-[5-ethyl-2-(4-trifluoromethylphenyl)oxazol-4-ylmethoxymethyl]cyclohexylmethoxy}-2-methylpropionic acid as yellow oil

Sources & evidence

ORD record
ord-f00344eae9a94c3b9394860dd7d46af6
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Reaction notes

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