Acetic Acid → 1-[(2-Ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-3-azetidinecarboxylic acid

HRID 1942738

반응식

HRID 1942738 반응식
[CH2:1]([C:3]1[C:10]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)=[N:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)[CH3:2].[NH:30]1[CH2:33][CH:32]([C:34]([OH:36])=[O:35])[CH2:31]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([C:3]1[C:10]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([C:26]([F:28])([F:29])[F:27])[CH:17]=3)=[N:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:30]1[CH2:33][CH:32]([C:34]([OH:36])=[O:35])[CH2:31]1)[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866590062-Ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}benzaldehyde

생성물 1

HCID 545767221-[(2-Ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-3-azetidinecarboxylic acid수율 19.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}benzaldehyde (D72) (60 mg), 3-azetidinecarboxylic acid (28.9 mg) and acetic acid (0.1 mL) in dichloromethane (DCM) (3 mL) stirred under nitrogen at room temperature for 1 h was added sodium triacetoxyborohydride (60.6 mg) in one charge. The reaction was stirred at room temperature overnight. The mixture was partitioned with DCM and water, washed with saturated brine and the organic phase was dried and evaporated, the residue was purified by Mass Directed AutoPrep to afford 1-[(2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-3-azetidinecarboxylic acid (E31) (14 mg). δH (DMSO-d6, 400 MHz): 1.06 (3H, t), 1.33 (6H, d), 2.73 (2H, m), 3.22 (5H, m), 3.63 (2H, s), 4.89 (1H, m), 7.26 (2H, m), 7.39 (1H, d), 7.45 (1H, d), 7.84 (1H, s), 8.15 (2H, m). δF (DMSO-d6, 376 MHz): −61.3. MS (ES): C26H27F3N2O3S requires 504. found 505.1 (M+H+).

후처리

  1. additioncharge
  2. customThe mixture was partitioned with DCM and water
  3. washwashed with saturated brine
  4. customthe organic phase was dried
  5. customevaporated
  6. customthe residue was purified by Mass Directed AutoPrep

출처 및 근거

ORD 기록
ord-da18134323cb406592fae6f52eb183eb
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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