HCID 88720606, compound → HCID 88720492, compound

HRID 1904039Notes

Reaction equation

HRID 1904039 reaction equation
C([O:14][C:15](=[O:73])[C@H:16]([CH2:35][S:36][CH2:37][CH:38]([O:55][C:56](=[O:72])[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][CH3:71])[CH2:39][CH2:40][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][CH3:54])[NH:17]C(=O)CCCCCCCCCCCCCCC)(C1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.C(Cl)Cl>[C:56]([O:72][NH:17][C@H:16]([C:15]([OH:14])=[O:73])[CH2:35][S:36][CH2:37][CH:38]([O:55][C:56](=[O:72])[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][CH3:71])[CH2:39][CH2:40][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][CH3:54])(=[O:55])[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][CH3:71]

Participants

4

Reactant 1

HCID 88720606HCID 88720606, compound

Product 1

HCID 88720492HCID 88720492, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.2 g of N-palmitoyl-S-[2-(R,S)-palmitoyloxyoctadecyl]-(L)-cysteine benzhydryl ester is dissolved at room temperature in a mixture of 0.4 ml of trifluoroacetic acid and 1.6 ml of methylene chloride and the mixture is allowed to react for 2 hours. The mixture is evaporated to dryness under reduced pressure, the residue is dissolved in chloroform and the chloroform layer is extracted several times with water. After drying with sodium sulfate and evaporation of the solvent there is obtained a crystalline residue, which is dissolved in 2 ml of hot petroleum ether. After addition of 2 ml of ligroin the solution is cooled to -10° and there are obtained crystals of the N-palmitoyloxy-S-[2(R,S)-palmitoyloxyoctadecyl]-(L)-cysteine of melting point 80°-83°.

Workup

  1. customto react for 2 hours
  2. customThe mixture is evaporated to dryness under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform
  4. extractionthe chloroform layer is extracted several times with water
  5. dry with materialAfter drying with sodium sulfate and evaporation of the solvent there
  6. customis obtained a crystalline residue, which
  7. temperatureis cooled to -10°

Sources & evidence

ORD record
ord-61913ab008ed47889a3d3d0b10b6e547
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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