Dicyclohexylcarbodiimide → HCID 19980018, compound

HRID 1461497Notes

Reaction equation

HRID 1461497 reaction equation
[C:1]([C:3]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[N:2].CC([O-])(C)C.[K+].[Cl:36][CH:37]([CH:41]([CH3:43])[CH3:42])[C:38](O)=[O:39].C1CCC(N=C=NC2CCCCC2)CC1>CN1C(=O)CCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOCC>[Cl:36][CH:37]([CH:41]([CH3:43])[CH3:42])[C:38]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH:6]3[CH2:7][CH2:8][C:3]([C:1]#[N:2])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:4][CH2:5]3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)=[O:39]

Participants

9

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 3134932-chloro-3-methylbutanoic acidHCID 19809977HCID 19809977, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19980018HCID 19980018, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5.3 g of p-[p-(4-cyano-4-octylcyclohexyl)-phenyl]phenol (obtainable by alkaline ether splitting from r-1-cyano-cis-4-(4'-propyloxybiphenyl-4-yl)-1-octylcyclohexane with potassium tert-butylate in NMP at 180°), 1.9 g of optically active 2-chloro-3-methylbutyric acid and 170 g of DMAP are suspended in 40 ml of CH2Cl2. 3.1 g of DCC in 5 ml of CH2Cl2 are then added dropwise at 0° and stirring is carried out for 12 hours at room temperature. After separating off the dicyclohexylurea and the usual working up, optically active 4'-(4-cyano-4-octylcyclohexyl)-biphenyl-4-yl 2-chloro-3-methylbutyrate is obtained, K 81 SA 138 I.

Workup

  1. customAfter separating off the dicyclohexylurea

Sources & evidence

ORD record
ord-9abc8a76351f4619a6c35170b0261553
Source dataset
uspto-grants-1991_12
Patent number
US05075032

Reaction notes

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