Acetic Acid → 3-(3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentylamino)propanoic acid

HRID 1172938Notes

Reaction equation

HRID 1172938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([CH:17]3[CH2:21][CH2:20][C:19](=O)[CH2:18]3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(O)(=O)C.[NH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].C([BH3-])#N.[Na+]>CO.ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([CH:17]3[CH2:21][CH2:20][CH:19]([NH:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:18]3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 5003444Sodium cyanoborohydrideHCID 595565403-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone

Product 1

HCID 532476613-(3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentylamino)propanoic acid

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a slurry of 3-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone (0.178 g, 0.555 mmol) in MeOH (6.94 ml) and DCE (6.94 ml) was added acetic acid (0.254 ml, 4.44 mmol) followed by 3-aminopropanoic acid (0.494 g, 5.55 mmol). After about 1 h sodium cyanoborohydride (0.017 g, 0.277 mmol) was added to the reaction mixture. After about 15 h the reaction mixture was filtered, rinsing with MeOH. The filtrate was concentrated in vacuo and purified by RP HPLC to provide 3-(3-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentylamino)propanoic acid. LCMS (Table 1, Method c) Rt=1.64 min, m/z 394 (M+H)+.

Workup

  1. filtrationAfter about 15 h the reaction mixture was filtered
  2. washrinsing with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by RP HPLC

Sources & evidence

ORD record
ord-8de21c5ad7c74b5fa34f0e8a2bc658a6
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

Loading…