Urea → HCID 11750219, compound

HRID 1883481Notes

Reaction equation

HRID 1883481 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[CH3:20][O:21][C:22](=[O:31])[C@@H:23]([NH2:30])[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C.ON1C(=O)C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.NC(N)=O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:20][O:21][C:22](=[O:31])[C@@H:23]([NH:30][C:11](=[O:13])[CH:10]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

9

Reactant 6

HCID 1176UreaHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 10678767Methyl (2S)-amino(cyclohexyl)acetateHCID 11414215HCID 11414215, compound

Product 1

HCID 11750219HCID 11750219, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-cyano-phenyl)-2-(R,S)-cyclohexyl-propionic acid (8.8 g, 34.2 mmol, prepared as described in example 1d), (S)-amino-cyclohexyl-acetic acid methyl ester (6.27 g, 36.6 mmol), diisopropylethylamine (6.8 ml, 40.0 mmol), 3-hydroxy-3H-benzo[d][1,2,3]triazin-4-one (1.40 g, 8.6 mmol), and dimethylformamide (200 ml) was cooled to 10° C. A solution of dicyclohexyl-carbodiimide (8.26 g, 40.0 mmol) in toluene (8 ml) was added dropwise over a period of 3 hours and the reaction mixture was stirred for 36 hours. The precipitated urea was sucked off and the filtrate was evaporated in vacuo. Crystallization from n-heptane/isopropanol gave 10.68 g of the desired product, which contained 1,3-dicyclohexyl-urea. The crude material was used without further purification. MS m/z: 411 (M+H)+.

Workup

  1. customthe filtrate was evaporated in vacuo
  2. customCrystallization from n-heptane/isopropanol

Sources & evidence

ORD record
ord-5850c0f7283749a6a2ddf21bc417cca7
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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