HCID 22826111, compound → HCID 22826112, compound

HRID 1904034Notes

Reaction equation

HRID 1904034 reaction equation
C([O:14][C:15](=[O:44])[C@H:16]([CH2:35][S:36][CH2:37][C@H:38]([OH:43])[C@H:39]([OH:42])[CH2:40][OH:41])[NH:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(C1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.C(Cl)Cl>[C:18]([NH:17][C@H:16]([C:15]([OH:44])=[O:14])[CH2:35][S:36][CH2:37][C@H:38]([OH:43])[C@H:39]([OH:42])[CH2:40][OH:41])(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 1

HCID 22826111HCID 22826111, compound

Product 1

HCID 22826112HCID 22826112, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.9 g of N-palmitoyl-S-[2(R),3(R),4-trihydroxybutyl]-(L)-cysteine-benzhydryl ester in a mixture of 3 ml of trifluoroacetic acid and 12 ml of methylene chloride is allowed to stand for 2 hours at room temperature. The reaction mixture is then evaporated to dryness; the residue is triturated with ice-water, filtered off with suction and the solid substance is dried. It is then extracted with ligroin, and recrystallised from acetone to yield colourless crystals of N-palmitoyl-S-[2(R),3(R),4-trihydroxy-butyl]-(L)-cysteine, m.p. 76°-76.5°, having the specific rotation [α]D20 =-5° (c=0.819, dioxane).

Workup

  1. customThe reaction mixture is then evaporated to dryness
  2. customthe residue is triturated with ice-water
  3. filtrationfiltered off with suction
  4. customthe solid substance is dried
  5. extractionIt is then extracted with ligroin
  6. customrecrystallised from acetone

Sources & evidence

ORD record
ord-4863bc47cc844aefad2f4dd3683cff10
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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