Dicyclohexylcarbodiimide → Nalpha-t-Butoxycarbonyl-D-alanyl-D-leucine

HRID 437331

Reaction equation

HRID 437331 reaction equation
C(OC([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.[C:17]([O:21][C:22]([NH:24][C@@H:25]([C:27]([OH:29])=O)[CH3:26])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[C:17]([O:21][C:22]([NH:24][C@@H:25]([C:27]([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:29])[CH3:26])=[O:23])([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 637604tert-Butoxycarbonyl-D-leucineHCID 637606BOC-D-alanine

Product 1

HCID 53724831Nalpha-t-Butoxycarbonyl-D-alanyl-D-leucine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Nα-t-Butoxycarbonyl-D-leucine resin (53 g., 42.9 mmol) is deprotected as in part (b), and Nα-t-butoxycarbonyl-D-alanine (8.5 g., 45 mmol) is added followed by the addition of dicyclohexylcarbodiimide, 9.3 g., 45 mmol in chloroform, after 15 to 30 minutes, followed by agitation for 18 hours. The product is separated by filtration and washed three times with dichloromethane, 250 ml., and dried.

Workup

  1. additionis added
  2. customThe product is separated by filtration
  3. washwashed three times with dichloromethane, 250 ml
  4. custom, and dried

Sources & evidence

ORD record
ord-a9f21c9effb14dcaa24c62b65729a608
Source dataset
uspto-grants-1977_06
Patent number
US04031071

Linked notes

Loading…