Methanol → HCID 88720606, compound

HRID 1904040Notes

Reaction equation

HRID 1904040 reaction equation
[C:1](Cl)(=[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].[CH:19]([O:32][C:33](=[O:74])[C@H:34]([CH2:53][S:54][CH2:55][CH:56]([OH:73])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[NH:35][C:36](=[O:52])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Cl)(Cl)Cl.CO>C(Cl)Cl.N1C=CC=CC=1>[CH:19]([O:32][C:33](=[O:74])[C@H:34]([CH2:53][S:54][CH2:55][CH:56]([O:73][C:1](=[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])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[NH:35][C:36](=[O:52])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 8206Palmitoyl chlorideHCID 70511491HCID 70511491, compound

Product 1

HCID 88720606HCID 88720606, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

0.56 ml of palmitic acid chloride in 5 ml of methylenechloride are added to 0.8 g of N-palmitoyl-S-[2-(R,S)-hydroxyoctadecyl]-(L)-cysteine benzhydryl ester in 5 ml of pyridine. After standing for 24 hours at room temperature the acylation is completed as can be detected by thin layer chromatography on silicagel Merck, chloroform 2 ml of methanol are added and after 20 minutes the reaction mixture is evaporated under reduced pressure. The residue is taken up in chloroform and the chloroform solution is extracted twice each time with 1 N HCl, saturated sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. After purification of the residue over 20 g of silicagel Merck with chloroform as eluant there are obtained colorless crystals of the N-palmitoyl-S-[2(R,S)-palmitoyloxyoctadecyl]-(L)-cysteine-benzhydryl ester, which can be crystallised from acetone-methanol and which melts at 46°-47°.

Workup

  1. additionare added and after 20 minutes the reaction mixture
  2. customis evaporated under reduced pressure
  3. extractionthe chloroform solution is extracted twice each time with 1 N HCl, saturated sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customAfter purification of the residue over 20 g of silicagel Merck with chloroform as eluant

Sources & evidence

ORD record
ord-3fece236fb7b4326b2f6e72b90f7473d
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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