Palmitic Acid → HCID 56632483, compound

HRID 1421199Notes

Reaction equation

HRID 1421199 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-2cb7723f8c1745b8b9fbc43f060dcd44
Source dataset
uspto-grants-2000_06
Patent number
US06074650

Reaction notes

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