Toluene → 2,2-Dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]-butyric acid

HRID 854672Notes

Reaction equation

HRID 854672 reaction equation
[CH3:1][C:2]([CH3:33])([CH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])[CH2:13]1)[C:3]([O:5]C(C)(C)C)=[O:4].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH3:1][C:2]([CH3:33])([CH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])[CH2:13]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69244352Tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate

Product 1

HCID 692435922,2-Dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]-butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

300 mg of tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate are dissolved in 20 ml of dichloromethane, and 10 ml of trifluoroacetic acid are added. The reaction mixture is stirred at room temperature for 1 hour. 200 ml of toluene are added and the solvents are then concentrated under reduced pressure. The residue is purified by RP-HPLC. This gives 180 mg of 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyric acid as an oil. C24H33NO4 (399.53), MS(ESI): 400 (M+H+).

Workup

  1. concentrationthe solvents are then concentrated under reduced pressure
  2. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-25287a217049415bbb8c4f51d4fb3452
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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