1,2-Dichloroethane → cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate

HRID 425024노트

반응식

HRID 425024 반응식
C(Cl)CCl.[CH3:5][C:6]([O:9][C:10]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[CH2:14][CH:15]=[CH2:16])=[O:11])([CH3:8])[CH3:7].[CH:20]1(O)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:6]([O:9][C:10]([NH:12][C@@H:13]([CH2:14][CH:15]=[CH2:16])[C:17]([O:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18])=[O:11])([CH3:5])([CH3:7])[CH3:8]

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acid

생성물 1

HCID 58150165cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate수율 68.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of DMAP (0.057 g, 0.465 mmol) in DCM (20 ml) was added EDC (0.980 g, 5.11 mmol). A solution of Boc-L-allylglycine (1.0 g, 4.65 mmol) in DCM (5 ml) was added and the mixture stirred for 20 minutes at RT. Cyclopentanol (0.506 ml, 5.58 mmol) was then added and the mixture stirred overnight at RT for complete reaction. After concentration of the reaction solvent in vacuo, the residue was subjected to column chromatography eluting with 6% EtOAc in hexanes. Yield=0.907 g, 3.20 mmol, 68.9% yield. m/z 284 [M+H]+.

후처리

  1. stirringthe mixture stirred overnight at RT for complete reaction
  2. washeluting with 6% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-8590790181434f2494ad1806c81d8ba9
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106091B2

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