1,2-Dichloroethane → HCID 178450645, compound

HRID 1717702Notes

Reaction equation

HRID 1717702 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](O)=[O:39])=[CH:33][CH:32]=1)([CH3:30])[CH3:29].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C([O-])(O)=O.[Na+]>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:38](=[O:39])[CH2:37][C:34]2[CH:35]=[CH:36][C:31]([CH:28]([CH3:29])[CH3:30])=[CH:32][CH:33]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 782304-Isopropylphenylacetic acidHCID 81531DiisopropylethylamineHCID 178450643HCID 178450643, compound

Product 1

HCID 178450645HCID 178450645, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of enantiomer A of butyl 1-[(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate, (41 mg, 0.11 mmol) in CH2CL2 (3 mL) was added (4-isopropylphenyl)acetic acid (98 mg, 0.55 mmol), EDC (105 mg, 0.55 mmol), HOBt (74 mg, 0.55 mmol) and DIEA (200 μL, 1.10 mmol). After stirring at room temperature for 18 h, the reaction mixture was poured into saturated aqueous NaHCO3 (10 mL) and extracted with EtOAc (20 mL). The organic layer was washed with brine (2×10 mL), dried over Na2SO4, filtered and concentrated. Chromatography (10% EtOAc in Hexane) gave butyl 1-{(trans-4-tert-butylcyclohexyl)[(4-isopropylphenyl)acetyl]amino}indane-5-carboxylate. HPLC/MS: m/z=532.3 (M+1), Rt=3.15 min.

Workup

  1. extractionextracted with EtOAc (20 mL)
  2. washThe organic layer was washed with brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75b336d0194541c7a6a5c415d8ff13ee
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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