Triethylamine → (R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl ester

HRID 1915

反応式

HRID 1915 の反応式
[CH2:1]([O:4][C:5](=[O:16])[C@@H:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:24]([NH:34][C:35]([CH3:40])([C:37](O)=[O:38])[CH3:36])([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:1]([O:4][C:5](=[O:16])[C@H:6]([NH:7][C:37](=[O:38])[C:35]([NH:34][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([CH3:40])[CH3:36])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 22883347D-Homophenylalanine allyl ester

生成物 1

HCID 67666530(R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl ester収率 69.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultant homogenous yellow solution quenched by addition of brine. The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride layers dried over powdered anhydrous magnesium sulfate. Filtration of the methylene chloride solution to remove the spent drying agent followed by evaporation of solvent afforded an oil which was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant. The desired product (419 mg; 69.7%) was isolated as a white amorphous solid. FAB-MS:- calculated for C25 H30N2O5 438.2; found 439.3 (M+1).

後処理

  1. customthe resultant homogenous yellow solution quenched by addition of brine
  2. extractionThe two phase system was extracted with methylene chloride (2×25 ml)
  3. dry with materialthe combined methylene chloride layers dried
  4. filtrationFiltration of the methylene chloride solution
  5. customto remove the
  6. customspent drying agent
  7. customfollowed by evaporation of solvent
  8. customafforded an oil which
  9. customwas purified by column chromatography on silica gel using
  10. additiona solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant

出典と根拠

ORDレコード
ord-2788899244b0487da69285b0cbf52602
出典データセット
uspto-grants-1998_03
特許番号
US05726319

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