Palmitic Acid → HCID 56632483, compound

HRID 377140Notes

Reaction equation

HRID 377140 reaction equation
[C:1]([OH:18])(=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][CH3:16].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1.[C:43]([O:47][C:48](=[O:70])[C@H:49]([CH2:68][SH:69])[NH:50][C:51](=[O:67])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])([CH3:46])([CH3:45])[CH3:44]>C(Cl)(Cl)Cl>[C:43]([O:47][C:48](=[O:70])[C@H:49]([CH2:68][S:69][C:1](=[O:18])[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])[NH:50][C:51](=[O:67])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])([CH3:44])([CH3:45])[CH3:46]

Participants

6

Reactant 4

HCID 985Palmitic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 13886660HCID 13886660, compound

Product 1

HCID 56632483HCID 56632483, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Palmitic acid (2.5 g, 9.6 mmol), dimethylaminopyridine (130 mg, 0.9 mmol) and dicyclohexylcarbodiimide (9.6 mmol) are dissolved in 100 ml of chloroform. The solution is stirred for half an hour and N-palmitoylcysteine tert.-butyl ester (2 g, 4.8 mmol), which has previously been dissolved in 50 ml of chloroform, is added dropwise to the other solution. After 11/2 h, the solvent is removed in a rotary evaporator, and the residue is taken up in 100 ml of chloroform/methanol 1:5. The product forms a voluminous precipitate at -20 degrees C. It is filtered off with suction and dried under high vacuum.

Workup

  1. additionis added dropwise to the other solution
  2. customAfter 11/2 h, the solvent is removed in a rotary evaporator
  3. customat -20 degrees C
  4. filtrationIt is filtered off with suction
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-43ea6a5dbb0a4490adf4dd5667248e7a
Source dataset
uspto-grants-2000_02
Patent number
US06024964

Reaction notes

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