1,2-Dichloroethane → Ethyl 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoate

HRID 882852ノート

反応式

HRID 882852 の反応式
[CH:1]1C=CC2N(O)N=NC=2[CH:6]=1.CCN(CC)CC.[C:18]([O:22][C:23]([NH:25][CH:26]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:27]([OH:31])[C:28]([OH:30])=[O:29])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(N)CC1.C(Cl)CCl>C(Cl)Cl>[C:18]([O:22][C:23]([NH:25][CH:26]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH:27]([OH:31])[C:28]([O:30][CH2:1][CH3:6])=[O:29])=[O:24])([CH3:21])([CH3:19])[CH3:20]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471Triethylamine2 回HCID 69828Cyclopropylamine2 回HCID 757711-Hydroxybenzotriazole2 回HCID 34203793-tert-Butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

生成物 1

HCID 67095085Ethyl 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoate収率 87.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

74.2 Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate EDC (8.3 g, 43.3 mmol), HOBT (6.6 g, 43.1 mmol) and Et3N (7 ml, 50.2 mmol) were added to a mixture of 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (10.6 g, 35.9 mmol) and cyclopropylamine (3.3 ml, 47.6 mmol) in DCM (300 mL) at 5° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. After cooling to 5° C. more cyclopropylamine (2 ml, 28.5 mmol), EDC (5 g, 26.1 mmol), HOBT (4 g, 26.1 mmol) and Et3N (3.5 ml, 25.1 mmol) were added, the mixture was allowed to warm to room temperature and the stirring was continued overnight. DCM (300 mL) was added, followed by washing with 0.5 M aqueous HCl solution, brine and drying with MgSO4. The crude product was recrystallized from methyl-tert-butylether, the crystals obtained were washed with n-pentane and dried providing the title compound (10.2 g, 85%).

後処理

  1. additionwere added
  2. temperatureto warm to room temperature
  3. waitthe stirring was continued overnight
  4. washby washing with 0.5 M aqueous HCl solution, brine
  5. dry with materialdrying with MgSO4
  6. customThe crude product was recrystallized from methyl-tert-butylether
  7. customthe crystals obtained
  8. washwere washed with n-pentane
  9. customdried

出典と根拠

ORDレコード
ord-310840171c074fada23db26edd44e120
出典データセット
uspto-grants-2012_08
特許番号
US08236798B2

反応ノート

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