1,2-Dichloroethane → HCID 68747186, compound

HRID 333309Notes

Reaction equation

HRID 333309 reaction equation
[NH2:1][CH2:2][CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH2:20]([O:27][C:28](=[O:38])[CH2:29][C:30]1([C:35](O)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[NH4+].[OH-]>CN(C=O)C.O.CCOC(C)=O>[CH2:20]([O:27][C:28](=[O:38])[CH2:29][C:30]1([C:35]([NH:1][CH2:2][CH:3]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:4]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:5])=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 181649HOAtHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 68749931HCID 68749931, compound

Product 1

HCID 68747186HCID 68747186, compoundYield 58.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-amino-2-(4-methoxybenzyl)propanoate (50 mg, 0.188 mmol), 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (49.4 mg, 0.188 mmol), EDC (47.0 mg, 0.245 mmol) and HOAt (33.3 mg, 0.245 mmol) in DMF (2 ml) was allowed to stir at room temperature for 3 hours. The reaction mixture was diluted with H2O and EtOAc. To the organic layer was added NH4OH (6 ml) and washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50) to give tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(4-methoxybenzyl)propanoate (56.3 mg); Retention time=1.61 minutes (condition B); MS (m+1)=510.5; 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9H) 1.57-1.70 (m, 6H) 2.00-2.04 (m, 2H) 2.66-2.86 (m, 5H) 3.24-3.47 (m, 2H) 3.77 (s, 3H) 5.08 (s, 2H) 6.36-6.39 (m, 1H) 6.79-6.82 (m, 2H) 7.07-7.11 (m, 2H) 7.30-7.34 (m, 5H).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50)

Sources & evidence

ORD record
ord-828d46e017ac40c892cfa10968caa45e
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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