Ethanolamine → (9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate

HRID 1940869Notes

Reaction equation

HRID 1940869 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].[CH2:7]([CH2:9][NH2:10])[OH:8].ON1[C:16](=O)[CH2:15][CH2:14][C:13]1=O.O1[CH2:24][CH2:23]OCC1>O>[CH:13]1[C:13]2[CH:23]([CH2:24][O:4][C:1]([NH:10][CH2:9][CH2:7][OH:8])=[O:2])[C:16]3[C:15](=[CH:16][CH:13]=[CH:14][CH:15]=3)[C:14]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 80170N-Hydroxysuccinimide

Product 1

HCID 2817739(9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

68.0 g (ca 200 mMol) 9-fluorenylmethoxycarbonyl-N-hydroxysuccinimide ester (Fmoc-O-Su) is dissolved with stirring in 300 ml dioxan in a 1 l round-bottomed flask. 40 g Na2CO3 dissolved in 200 ml water as well as 14.4 ml (238 mMol) ethanolamine are added successively to the clear solution. The pulpy reaction mixture which forms at once is stirred overnight at room temperature and is aspirated on the following day. The filtration residue which contains unreacted Fmoc-O-Su, N-hydroxy-succinimide as well as the desired product, is re-crystallized from ethyl acetate. After drying in a vacuum 47.4 g pure product=76% of the theoretical yield are obtained.

Workup

  1. additionare added successively to the clear solution
  2. customThe pulpy reaction mixture which

Sources & evidence

ORD record
ord-811cdd26e34a4da888583c53a5c70042
Source dataset
uspto-grants-1997_12
Patent number
US05700919

Reaction notes

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