Trifluoroacetic acid → (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyric acid trifluoroacetic acid salt

HRID 854654Notes

Reaction equation

HRID 854654 reaction equation
[CH3:1][CH:2]([CH3:34])[C@H:3]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([O:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])[CH2:14]1)[C:4]([O:6]C(C)(C)C)=[O:5].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(O)=O>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[CH3:1][CH:2]([CH3:34])[C@H:3]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([O:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[O:24][C:25]=2[CH3:26])[CH2:14]1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86597944tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate

Product 1

HCID 69243866(S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyric acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate are dissolved in 1 ml of formic acid, and 0.5 ml of trifluoroacetic acid is added. The solution is stirred at room temperature for 18 and then concentrated completely. The residue is purified by HPLC, which gives 28.2 mg of (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyric acid trifluoroacetic acid salt as a colorless solid. C24H34N2O2.C2HF3O2 (414.55); MS (ES−): 413.28 (M+−H).

Workup

  1. concentrationconcentrated completely
  2. customThe residue is purified by HPLC, which

Sources & evidence

ORD record
ord-45f5afa20a6740a38838ca062c96af86
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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