1,2-Dichloroethane → HCID 86679488、化合物

HRID 1776529ノート

反応式

HRID 1776529 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[N:15]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[S:16]([CH3:19])(=[O:18])=[O:17])[C:9]([O-:11])=[O:10])[CH2:3][CH2:2]1.[Li+].C(Cl)CCl.O[CH2:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[N:15]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)[S:16]([CH3:19])(=[O:17])=[O:18])[C:9]([O:11][CH2:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=[O:10])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 86679486HCID 86679486、化合物

生成物 1

HCID 86679488HCID 86679488、化合物収率 76%

試薬・触媒・溶媒 2

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

実験手順

To a solution of lithium 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)benzoate (theoric 0.869 mmol) and EDC (349 mg, 1.821 mmol) in dry DCM (3 ml), benzyl 2-hydroxyacetate (151 mg, 0.910 mmol) and DMAP (111 mg, 0.910 mmol) were added at RT. The final mixture was stirred for 2 days, then the solvent was evaporated, the residue was portioned between water and EtOAc, the organic layer was washed with NaHCO3 sat. sol. and brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32% NH4OH 95/5/0.5) to give 2-(benzyloxy)-2-oxoethyl 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)-methylsulfonamido)benzoate as a colorless oil (370 mg, 0.661 mmol, 76% yield over 2 steps, MS/ESI+ 560.1 [MH]+).

後処理

  1. customthe solvent was evaporated
  2. washthe organic layer was washed with NaHCO3 sat. sol. and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32% NH4OH 95/5/0.5)

出典と根拠

ORDレコード
ord-06d74321ddf942da8cd4d0e3f31a32c3
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

読み込み中…