Potassium Carbonate → (R)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-3-(dodecyloxy)-2-hydroxypropyl)thio)propanoate

HRID 2407934ノート

反応式

HRID 2407934 の反応式
[CH2:1]([O:13][CH2:14][C@@H:15]1[CH2:17][O:16]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([NH:35][C@@H:36]([CH2:44][SH:45])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[CH:27]1[C:28]2[CH:29]([CH2:31][O:32][C:33]([NH:35][C@@H:36]([CH2:44][S:45][CH2:17][C@H:15]([OH:16])[CH2:14][O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])=[O:34])[C:30]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11440950(R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-mercaptopropanoateHCID 86678312(S)-2-((dodecyloxy)methyl)oxirane

生成物 1

HCID 71294546(R)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-3-(dodecyloxy)-2-hydroxypropyl)thio)propanoate

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A solution of (S)-2-((dodecyloxy)methyl)oxirane (1.1 eq), (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate (8, 1 eq) and 1M K2CO3 (1.1 eq) in tBuOH (0.1 M) was stirred at 25° C. for 15 hours. The reaction mixture was concentrated en vaccuo to remove tBuOH and dissolved in EtOAc. The EtOAc solution was washed three times with water, and once with brine. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-30% EtOAc/Hex to give the title product as a colorless viscous oil.

後処理

  1. concentrationThe reaction mixture was concentrated en vaccuo
  2. customto remove tBuOH
  3. dissolutiondissolved in EtOAc
  4. washThe EtOAc solution was washed three times with water
  5. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-eb22327682fc401799d2a01a9dadcd8b
出典データセット
uspto-grants-2014_08
特許番号
US08808703B2

反応ノート

読み込み中…