HCID 69243891, compound → HCID 69242949, compound

HRID 854648Notes

Reaction equation

HRID 854648 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][O:23][C:24]2([C:29]([O:31]C(C)(C)C)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:17]1>FC(F)(F)C(O)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][O:23][C:24]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:17]1

Participants

3

Reactant 1

HCID 69243891HCID 69243891, compound

Product 1

HCID 69242949HCID 69242949, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

20 mg of impure tert-butyl 1-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexylmethoxy]cyclopentanecarboxylate is stirred in 1 ml of trifluoroacetic acid at room temperature overnight. The solution is concentrated completely and the residue is chromatographed on silica gel (heptane/ethyl acetate 10/1->1/1->methyl tert-butyl ether), giving 7.5 mg of 1-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]cyclo-pentanecarboxylic acid. C25H33NO5 (427.55); LCMS 428.2 (MH+).

Workup

  1. concentrationThe solution is concentrated completely
  2. customthe residue is chromatographed on silica gel (heptane/ethyl acetate 10/1->1/1->methyl tert-butyl ether)

Sources & evidence

ORD record
ord-5730315492ad4347bd6bc966dc291a1a
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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