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

HRID 2407934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407934
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-eb22327682fc401799d2a01a9dadcd8b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08808703B2

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