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

HRID 425024ノート

反応式

HRID 425024 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-8590790181434f2494ad1806c81d8ba9
出典データセット
uspto-grants-2012_01
特許番号
US08106091B2

反応ノート

読み込み中…