Pyridine → (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

HRID 854655Notes

Reaction equation

HRID 854655 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][CH:12]([CH3:44])[C@H:13]([NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C:14]([O:16]C(C)(C)C)=[O:15]>ClCCl.O>[C:1]([N:21]([CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C@@H:13]([CH:12]([CH3:44])[CH3:11])[C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86597944tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate

Product 1

HCID 69240762(S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

12 μl of acetyl chloride and 22 μl of pyridine are added to 40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate in 0.5 ml of dichloromethane, and the mixture is stirred at room temperature for 18 h. The solution is then diluted with water and dichloromethane, the aqueous phase is removed and extracted with dichloromethane and the combined phases are dried over MgSO4 and concentrated. The residue is taken up in 0.5 ml of trifluoroacetic acid and allowed to stand at room temperature overnight. The solvent is distilled off completely and the residue is purified by HPLC, which gives 17 mg of (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid. C26H36N2O5 (456.59); LCMS (ESI): 457.36 (MH+).

Workup

  1. customthe aqueous phase is removed
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined phases are dried over MgSO4
  4. concentrationconcentrated
  5. waitto stand at room temperature overnight
  6. distillationThe solvent is distilled off completely
  7. customthe residue is purified by HPLC, which

Sources & evidence

ORD record
ord-ff110fff65a849a78a16d274d5843534
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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