Acetic Acid → (S)-5-(9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid methyl ester

HRID 507099노트

반응식

HRID 507099 반응식
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([C@@H:14]1[C:20]2=[CH:21][C:22]3[CH2:23][O:24][CH2:25][C:26]=3[CH:27]=[C:19]2[NH:18][CH2:17][CH2:16][CH2:15]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH3:37][O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:46])([CH3:45])[CH2:42][CH:43]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[CH3:37][O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:46])([CH3:45])[CH2:42][CH2:43][N:18]1[C:19]2[C:20](=[CH:21][C:22]3[CH2:23][O:24][CH2:25][C:26]=3[CH:27]=2)[C@@H:14]([N:7]([CH2:6][C:5]2[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:3]([C:2]([F:1])([F:35])[F:36])[CH:4]=2)[C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)[CH2:15][CH2:16][CH2:17]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 3018723Methyl 3,3-dimethyl-5-oxovalerateHCID 5049666Sodium triacetoxyborohydrideHCID 59432492(S)-(3,5-bis-trifluoromethyl-benzyl)-(3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

생성물 1

HCID 59432400(S)-5-(9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid methyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of (S)-(3,5-bis-trifluoromethyl-benzyl)-(3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (0.195 mmol) in dichloroethane (5 mL), add 3,3-dimethyl-5-oxo-pentanoic acid methyl ester (0.585 mmol) along with a catalytic amount of acetic acid. To this stirred solution add sodium triacetoxyborohydride (0.975 mmol). After stirring for 12 h, quench the reaction with aqueous sodium carbonate (5 mL) and dilute with dichloromethane (5 mL). Dry the organic portion, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (2-35%) to afford the title compound as a colorless oil. MS (ES+): 655.2 (M+H).

후처리

  1. customquench
  2. customthe reaction with aqueous sodium carbonate (5 mL)
  3. customDry the organic portion
  4. filtrationfilter
  5. customremove the solvent under vacuum
  6. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (2-35%)

출처 및 근거

ORD 기록
ord-25c356207a4a4ff9b4c45ac01034a2c3
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786108B2

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