Potassium Carbonate → N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine

HRID 1904038Notes

Reaction equation

HRID 1904038 reaction equation
[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][SH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[O:25]1[C:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][S:21][CH2:26][CH:27]([OH:25])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12151201L-Cysteine, N-(1-oxohexadecyl)-HCID 202138261,2-Epoxyoctadecene

Product 1

HCID 88720815N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.6 g of N-palmitoylcysteine, 5 g of 1,2-epoxy-octadecene and 5.35 g of potassium carbonate in 100 ml ethanol are heated in an atmosphere of nitrogen at 80° for 15 hours. After evaporation, HCl is added so as to obtain a pH of about 3 and the mixture is extracted with chloroform. The chloroform extract is washed with water and is then dried with sodium sulfate. After evaporation there is obtained a colorless residue which is recrystallized from ethyl acetate. There are obtained colorless crystals of the N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine of melting point 96°-98° [α]D20 =+16° (c=0.78, chloroform).

Workup

  1. customAfter evaporation, HCl
  2. additionis added so as
  3. customto obtain a pH of about 3
  4. extractionthe mixture is extracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. dry with materialis then dried with sodium sulfate
  8. customAfter evaporation
  9. customthere is obtained a colorless residue which
  10. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b9653f24c63d40849e360c03a413caca
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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