Diisopropylcarbodiimide → 3-(2-Biphenyl-4-yl-ethylcarbamoyl)-2-phenethyl-pentanedioic acid 5-tertbutyl ester 1-methyl ester

HRID 902922

反応式

HRID 902922 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH:4]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:5]([C:14]([OH:16])=O)[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C1C=C[C:29]2N(O)N=[N:32][C:30]=2C=1.[C:36]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37](CCN)=[CH:38][CH:39]=[CH:40][CH:41]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[CH:4]([CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:5]([C:14](=[O:16])[NH:32][CH2:30][CH2:29][C:48]1[CH:47]=[CH:46][C:45]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:50][CH:49]=1)[CH2:6][C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8]

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 219212422-([1,1'-Biphenyl]-2-yl)ethanamineHCID 69212314HCID 69212314、化合物

生成物 1

HCID 692094683-(2-Biphenyl-4-yl-ethylcarbamoyl)-2-phenethyl-pentanedioic acid 5-tertbutyl ester 1-methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of the compound of example 53 (590 mg, 1.68 mmol) and HOBt (272 mg, 2.016 mmol) in anhydrous DMF was stirred in an ice bath for 10 minutes. Biphenyl ethylamine (404 mg, 2.02 mmol) was added followed by the addition of DIC (320 μL, 2.01 mmol). After 20 minutes, the ice bath was removed and stirring was continued at room temperature. After 24 h of stirring, the reaction mixture was partitioned between ethyl acetate and HCl (1M, excess). The aqueous phase was extracted several times with ethyl acetate. The recombined organic layer was extracted with brine, saturated sodium hydrogen carbonate, and brine. The solvent was evaporated following drying over sodium sulfate and filtration. The crude was flashed using 25% EtOAc in hexanes. 1H-NMR(CDCl3, 300 MHz: 1.41(s, 9H); 1.82(m, 2H); 2.23(m, 1H); 2.55(t, J=8.1 Hz, 2H); 2.75(m, 5H); 3.54(m, 1H); 3.70(s, 3H); 6.09(t, J=5.7 Hz, 1H); 7.13-7.36, 7.41-7.49, 7.55-7.58(m, 14H).

後処理

  1. customthe ice bath was removed
  2. customwas continued at room temperature
  3. stirringAfter 24 h of stirring
  4. customthe reaction mixture was partitioned between ethyl acetate and HCl (1M, excess)
  5. extractionThe aqueous phase was extracted several times with ethyl acetate
  6. extractionThe recombined organic layer was extracted with brine, saturated sodium hydrogen carbonate, and brine
  7. customThe solvent was evaporated
  8. dry with materialfollowing drying over sodium sulfate and filtration

出典と根拠

ORDレコード
ord-7b2295d010ff4a6dae3bc37439442802
出典データセット
uspto-grants-2008_04
特許番号
US07365091B2

関連ノート

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