Dicyclohexylcarbodiimide → N-(N'-Acetylglycyl) sphingosine

HRID 482127Notes

Reaction equation

HRID 482127 reaction equation
[OH:1][CH2:2][C@@H:3]([C@@H:5](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[OH:6])[NH2:4].[C:22]([NH:25][CH2:26][C:27](O)=[O:28])(=[O:24])[CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[C:22]([NH:25][CH2:26][C:27]([NH:4][C@H:3]([C@@H:5](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[OH:6])[CH2:2][OH:1])=[O:28])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 5280335Sphingosine

Product 1

HCID 86749485N-(N'-Acetylglycyl) sphingosine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.0 gr of sphingosine (16.70 mM), prepared according to Example 4, 2.1 gr of N-acetylglycine (18.37 mM) and 3.8 gr of dicyclohexylcarbodiimide (18.40 mM) are left to react in 150 cc of chloroform, under warm conditions overnight. The reaction mixture is placed in a freezer to precipitate. The urea is filtered, and the chloroform solution is washed with H2O. The raw material is purified by chromatography using a mixture of CH2Cl2 /ethyl acetate/CH3OH, 70:30:10 v/v/v.

Workup

  1. waitare left
  2. customto precipitate
  3. filtrationThe urea is filtered
  4. washthe chloroform solution is washed with H2O
  5. customThe raw material is purified by chromatography
  6. additiona mixture of CH2Cl2 /ethyl acetate/CH3OH, 70:30:10 v/v/v

Sources & evidence

ORD record
ord-a8a5b36237b34e708ce4fddf06792b27
Source dataset
uspto-grants-1998_08
Patent number
US05792858

Reaction notes

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