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

HRID 2205039ノート

反応式

HRID 2205039 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-dfd8dde0da41401590128f9b83f222ed
出典データセット
uspto-grants-2016_06
特許番号
US09365506B2

反応ノート

読み込み中…