Urea → HCID 131723233, compound

HRID 1937818Notes

Reaction equation

HRID 1937818 reaction equation
[CH2:1]([NH:8][C:9](=[O:23])[CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:35])[C@@H:27]([NH2:34])[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]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>[CH3:24][O:25][C:26](=[O:35])[C@@H:27]([NH:34][C:11](=[O:12])[CH:10]([C:9](=[O:23])[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

9

Reactant 6

HCID 1176UreaHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 10678767Methyl (2S)-amino(cyclohexyl)acetateHCID 22667623HCID 22667623, compound

Product 1

HCID 131723233HCID 131723233, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-benzyl-2-(R,S)-(4-cyano-benzyl)-malonamic acid (10 g, 32.4 mmol), (S)-amino-cyclohexyl-acetic acid methyl ester (5.94 g, 34.7 mmol), diisopropylethyl-amine (6.45 ml, 37.9 mmol), 3-hydroxy-3H-benzo[d][1,2,3]triazin-4-one (1.32 g, 8.1 mmol), and dimethylformamide (100 ml) was cooled to 10° C. A solution of dicyclohexyl-carbodiimide (7.83 g, 37.9 mmol) in toluene (10 ml) was added dropwise and the reaction mixture stand over night. The precipitated urea was sucked off, the filtrate was evaporated in vacuo, solved in ethyl acetate, washed with saturated sodium hydrogen carbonate-solution and brine, dried, and evaporated in vacuo. Crystallization from n-heptane/isopropanol gave 9.91 g (66%) of the desired product. mp.: 170-174° C., MS m/z: 462 (M+H)+.

Workup

  1. waitthe reaction mixture stand over night
  2. customthe filtrate was evaporated in vacuo
  3. washwashed with saturated sodium hydrogen carbonate-solution and brine
  4. customdried
  5. customevaporated in vacuo
  6. customCrystallization from n-heptane/isopropanol

Sources & evidence

ORD record
ord-d6490bc120044e748546c4d3635f0a3c
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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