Dicyclohexylcarbodiimide → palmitoyl-L-Ala-D-Glu(OSu)OBzl

HRID 2164471Notes

Reaction equation

HRID 2164471 reaction equation
[NH:1]([C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:24])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].O[N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(Cl)(Cl)Cl>[NH:1]([C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:24])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:11])[O:12][N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47])=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131714154palmitoyl-L-Ala-D-Glu(OH)OBzl

Product 1

HCID 131714153palmitoyl-L-Ala-D-Glu(OSu)OBzlYield 78.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1) (1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with chloroform. The filtrate was concentrated in vacuo and the diisopropylether was added to the residue. The product was collected and dried to afford palmitoyl-L-Ala-D-Glu(OSu)OBzl (2)(1.70 g).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe diisopropylether was added to the residue
  5. customThe product was collected
  6. customdried

Sources & evidence

ORD record
ord-1966a6fedb5b4d5ea03c50f1d84a6fdd
Source dataset
uspto-grants-1985_03
Patent number
US04504584

Reaction notes

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