Ethanol → H-Lys(Z)-OL

HRID 47742Notes

Reaction equation

HRID 47742 reaction equation
C(OC([NH:8][C@H:9]([CH2:25][OH:26])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(O)C>O>[NH2:8][C@H:9]([CH2:25][OH:26])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 10915530Boc-Lysinol(Z)

Product 1

HCID 18603233H-Lys(Z)-OLYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4 g of benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate, 30 cm3 of trifluoroacetic acid and 20 cm3 of ethanol is stirred at a temperature in the region of 20° C. for 2 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 50 cm3 of water and washed with twice 100 cm3 of diethyl ether. The aqueous phase is separated out after settling has taken place, basified with sodium carbonate to pH 9-10 and then extracted with 3 times 100 cm3 of dichloromethane. The combined extracts are washed with aqueous sodium chloride solution and then dried on magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.0 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate are obtained in the form of a white solid melting at 82° C.

Workup

  1. customAfter concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained
  2. washwashed with twice 100 cm3 of diethyl ether
  3. customThe aqueous phase is separated out after settling
  4. extractionextracted with 3 times 100 cm3 of dichloromethane
  5. washThe combined extracts are washed with aqueous sodium chloride solution
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-d04adf6bf50843f4bbd0cdf78372fd9e
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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