Diisopropylcarbodiimide → HCID 66621431, compound

HRID 414911Notes

Reaction equation

HRID 414911 reaction equation
FC1C=CC=CC=1CCN[C:11]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12].[CH2:19]([C:26]1([N:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(N=C=NC(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)C>[CH2:19]([C:26]1([N:33]([CH3:34])[CH3:35])[CH2:31][CH2:30][CH:29]([NH:32][C:11](=[O:12])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 43529530HCID 43529530, compoundHCID 66621223HCID 66621223, compound

Product 1

HCID 66621431HCID 66621431, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

As described for Example 341, 0.95 mg 4-[2-(2-fluorophenyl)ethylcarbamoyl]butyric acid and 0.87 1-benzyl-N,N-dimethylcyclohexane-1,4-diamine were converted in 5 ml DMF in the presence of 0.59 ml N,N-diisopropylcarbodiimide and 0.50 g 1-hydroxybenzotriazole and the crude product (1.65 g yellow solid) similarly isolated. 720 mg of the non-polar diastereoisomer of glutaric acid (4-benzyl-4-dimethylaminocyclohexyl)amide was obtained by column chromatography on silica gel (3.0×20 cm) with 450 ml diethyl ether, followed by 450 ml diethyl ether/methanol (V:V=4:1) and 450 ml diethyl ether/methanol (V:V=1:1), was dissolved in 25 ml 2-butanone, 25 ml ethyl acetate and converted into the corresponding hydrochloride by adding 28 μl water and 198 μl chlorotrimethylsilane (657 mg of vitreous solid).

Workup

  1. customthe crude product (1.65 g yellow solid) similarly isolated

Sources & evidence

ORD record
ord-0620ed07bf5849339b737e7f748f1134
Source dataset
uspto-grants-2012_01
Patent number
US08088763B2

Reaction notes

Loading…