Chloroform → HCID 56631556, compound

HRID 1904041Notes

Reaction equation

HRID 1904041 reaction equation
[CH2:1](OS(C1C=CC(C)=CC=1)(=O)=O)[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].[C:40]([NH:57][C@H:58]([C:61]([OH:63])=[O:62])[CH2:59][SH:60])(=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55].C(Cl)(Cl)Cl>C(O)C.O>[C:40]([NH:57][C@H:58]([C:61]([OH:63])=[O:62])[CH2:59][S:60][CH2:1][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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 11145291Docosanyl-p-toluenesulfonateHCID 12151201L-Cysteine, N-(1-oxohexadecyl)-

Product 1

HCID 56631556HCID 56631556, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.8 g of docosanyl-p-toluenesulfonate and 5 g of potassium carbonate are added to 3.6 g of N-palmitoyl-(L)-cysteine in 50 ml of ethanol. The mixture is heated under stirring and in a nitrogen atmosphere at 80° for 20 hours. After evaporating to dryness the residue is acidified with 1 N HCl so as to obtain a pH of about 3 and then it is distributed between chloroform and water. After having dried and evaporated the chloroform layer a colourless crystalline residue is obtained, which is recrystallized from ethyl acetate. There is thus obtained the N-palmitoyl-S-docosanyl-(L)-cysteine.

Workup

  1. temperatureThe mixture is heated
  2. customAfter evaporating to dryness the residue
  3. customto obtain a pH of about 3
  4. customAfter having dried
  5. customevaporated the chloroform layer a colourless crystalline residue
  6. customis obtained
  7. customwhich is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-32474f89e7f5439ba93eeecf7509d264
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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