1,2-Dichloroethane → Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate

HRID 1908275노트

반응식

HRID 1908275 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>ClCCl>[CH:22]1([NH:25][C:11](=[O:13])[CH:10]([OH:14])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:24][CH2:23]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 34203793-tert-Butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

생성물 1

HCID 66645006Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate수율 114.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (3 g, 10.16 mmol), cyclopropanamine (780 μL, 11.26 mmol) in dichloromethane (70 ml) at 5° C. EDC (2.4 g, 12.52 mmol), HOBt (1.9 g, 12.41 mmol) and Et3N (3 ml, 21.52 mmol) were added and the mixture stirred at room temperature for 48 h. After completion of reaction dichloromethane (100 ml) was added, the solution washed with water and brine, dried, filtered off with suction and concentrated to give 3.9 g of a brown oil which was purified further via chromatography on silica gel (eluent: CH2Cl2+5-30% (v/v) methanol). After evaporation of the combined product fractions 0.82 g of a pale oil were obtained; ESI-MS [M-Boc+H]±: 235.1.

후처리

  1. customat 5° C
  2. additionwas added
  3. washthe solution washed with water and brine
  4. customdried
  5. filtrationfiltered off with suction
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-908b1fc04e6349fcbf64d8ff0c4dcf4c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598211B2

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