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

HRID 4423

Reaction equation

HRID 4423 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 7,846.1%

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)(170 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-34b5a02bca8a409287c4f086e8e5d348
Source dataset
uspto-grants-1988_02
Patent number
US04725582

Linked notes

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