1,2-Dichloroethane → HCID 131727750, compound

HRID 1434622Notes

Reaction equation

HRID 1434622 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:15]([NH:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][C@H:25]([C:29](O)=[O:30])[CH2:24]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:29]([C@@H:25]3[CH2:26][CH2:27][CH2:28][C@H:23]([NH:22][C:15](=[O:16])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:24]3)=[O:30])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 2755995rel-(1R,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acid

Product 1

HCID 131727750HCID 131727750, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3,4-dichlorophenyl)piperazine (350 mg, 1.51 mmol), cis-3-(N-Boc-amino)cyclohexane carboxylic acid (368 mg, 1.51 mmol), HOBt (209 mg, 1.51 mmol) and EDC (291 mg, 1.51 mmol) was added dichloromethane followed by TEA (153 mg, 1.51 mmoL). Upon completion of addition, the resulting solution was allowed to stir overnight. At the conclusion of this period, the reaction mixture was concentrated and then purified via silica gel chromatography (20% to 50% EtOAc/hexanes) to provide the title compound (640 mg) as an oil.

Workup

  1. additionUpon completion of addition
  2. concentrationAt the conclusion of this period, the reaction mixture was concentrated
  3. custompurified via silica gel chromatography (20% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3f86e3c8e65642b695f29fc4cb1e60a1
Source dataset
uspto-grants-2009_11
Patent number
US07615556B2

Reaction notes

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