Dicyclohexylcarbodiimide → Retinamide

HRID 429588

Reaction equation

HRID 429588 reaction equation
C1([N:7]=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33](O)=[O:34].ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33]([NH2:7])=[O:34]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 444795Retinoic Acid

Product 1

HCID 5370221RetinamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g (0.0146 mole) of dicyclohexylcarbodiimide (DCC) was added to the solution of 4.48 g (0.0112 mole) of 1-amino-polyethylene glyco (molecular weight 400), 3.98 g (0.0133 mole) of retinoic acid and 1.51 g (0.0112 mole) of 1 -hydroxybenzotriazole in 40 ml of dry dichloromethane, and the reaction solution was then treated according to the same procedure as described in Example 1(A) to obtain the title compound (Yield 62%, Tm=−14° C., Rf=0.15).

Workup

  1. additionthe reaction solution was then treated

Sources & evidence

ORD record
ord-b24423e0eff84616a3d65f696c31a5ff
Source dataset
uspto-grants-2001_11
Patent number
US06316644B1

Linked notes

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