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 507099ノート

反応式

HRID 507099 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-25c356207a4a4ff9b4c45ac01034a2c3
出典データセット
uspto-grants-2010_08
特許番号
US07786108B2

反応ノート

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