9-Phenyl-9-fluorenol → Nalpha-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

HRID 1275748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275748
[C:1]1([C:7]2([OH:20])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][C:23](=[O:45])[C@H:24]([CH2:43]O)[NH:25][C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27]>C1C=CC=CC=1.S(=O)(=O)(O)O>[CH3:21][O:22][C:23](=[O:45])[C@H:24]([CH2:43][O:20][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:25][C:26]([O:28][CH2:29][CH:30]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=2[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:27]

Komponenten

5

Edukt 2

HCID 1412279-Phenyl-9-fluorenolHCID 7020783(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate

Produkt 1

HCID 15516029Nalpha-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 6.2 g (24 mmol) of 9-phenyl-9H-fluoren-9-ol (Example 1b) and 6.8 g (20 mmol) of Nα -(9-fluorenylmethoxycarbonyl)-L-serine methyl ester in benzene (150 mL) was placed in a round bottomed flask fitted with a Dean-Stark trap. Two drops of concentrated sulfuric acid were added and the mixture heated under reflux with stirring for 1 h. Removal of the solvent under vacuo gave the crude Nα -(9-fluorenylmethoxycarbonyl)--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester which was subjected to the Fmoc deprotection in Step 2 without further purification.

Aufarbeitung

  1. customfitted with a Dean-Stark trap
  2. temperaturethe mixture heated
  3. temperatureunder reflux
  4. customRemoval of the solvent under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d66f290c649c46e1af7069af345a342b
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162824

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