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

HRID 854656Notes

Reaction equation

HRID 854656 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[CH3:9][CH:10]([CH3:42])[C@H:11]([NH:19][CH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([O:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])[CH2:22]1)[C:12]([O:14]C(C)(C)C)=[O:13].[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>CN(C=O)C>[F:46][C:45]([F:48])([F:47])[C:43]([OH:49])=[O:44].[CH3:3][N:19]([CH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([O:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)[O:32][C:33]=2[CH3:34])[CH2:22]1)[C@@H:11]([CH:10]([CH3:9])[CH3:42])[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86597944tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate

Product 1

HCID 69244322(S)-2-{methyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methyl-butyric acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 mg of methyl iodide and 12 mg of potassium carbonate are added to 40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-yl-methoxy)cyclohexylmethyl]amino}butyrate (see Example 42) in 0.5 ml of DMF, and the mixture is stirred at RT overnight. 1 ml of TFA is added to the reaction solution, and the mixture is stirred for a further 1 h. The solution is purified by preparative HPLC, yielding 6.4 mg of (S)-2-{methyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methyl-butyric acid trifluoroacetic acid salt. C25H36N2O4 (542.60); MS (ESI): 543 (MH+).

Workup

  1. stirringthe mixture is stirred for a further 1 h
  2. customThe solution is purified by preparative HPLC

Sources & evidence

ORD record
ord-ef57966f0fdc4a5d9570926e22e53e3e
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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