1,2-Dichloroethane → tert-butyl 4-(1-((1R,2R)-2-(benzyloxy)cyclohexyl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate

HRID 1685114Notes

Reaction equation

HRID 1685114 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:18]([C:26](O)=[O:27])[NH:17][C:16]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:53]1([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>CN(C=O)C.O>[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]1[C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:18]([C:26]([N:56]2[CH2:55][CH2:54][N:53]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:58][CH2:57]2)=[O:27])[NH:17][C:16]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 592923041-((1R,2R)-2-(benzyloxy)cyclohexyl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid2×

Product 1

HCID 59292285tert-butyl 4-(1-((1R,2R)-2-(benzyloxy)cyclohexyl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolved 15E (1.5 g, 3.82 mmol) in 15 mL of DMF and added EDC (1.28 g, 6.68 mmol) and HOBt (0.88 g, 6.49 mmol). The mixture was stirred for at least 15 minutes. Next, DIEA (2.0 mL, 11.4 mmol) was added along with tert-butyl piperazine-1-carboxylate (0.85 g, 4.58 mmol). This reaction mixture was then stirred overnight at RT. After the disappearance of 15E, this mixture was poured into 150 mL of water. The white solid was filtered, rinsed with water and dried under vacuum to provide tert-butyl 4-(1-((1R,2R)-2-(benzyloxy)cyclohexyl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate (15Ga) (1.6 g, 75%). ESI-MS: m/z 561.6 (M+H)+.

Workup

  1. stirringThis reaction mixture was then stirred overnight at RT
  2. filtrationThe white solid was filtered
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-78f8194512d34a87ad94423a32fe7025
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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