1,2-Dichloroethane → HCID 70006201, compound

HRID 1860532Notes

Reaction equation

HRID 1860532 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH:7]=[CH:8][Sn:9]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13])[C@@H:3]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].[CH:31](N(C(C)C)CC)(C)C.C(Cl)CCl>CN(C)C1C=CN=CC=1.ClCCl>[CH3:31][O:29][C:28](=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:3]1[C@H:4]([CH:7]=[CH:8][Sn:9]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][C:2]1=[O:1]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 70006814HCID 70006814, compound2×

Product 1

HCID 70006201HCID 70006201, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Wang resin bound trans-7-[2-Oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid. A dichloromethane (5 mL) solution of trans-7-[2-oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid of Step E (6.35 g, 12.05 mmol, 3 eq) was added to the Wang resin (5.66 g, 4.02 mmol, 1 eq) along with diisopropylethylamine (6.23 g, 48.20 mmol, 12 eq). The mixture was allowed to swell for 1 hour, and EDC (2.31 g, 12.05 mmol, 3 eq) was added followed by 4-dimethylaminopyridine (catalytic amount about 20 mg). The mixture was stirred at room temperature overnight. The resin was filtered, washed with dichloromethane (20 mL×2), repeatedly swollen with dichloromethane (20 mL) and shrunk with methanol (20 mL). The resin was washed with diethyl ether (20 mL×3) and dried on a filter funnel attached to a water aspirator for 30 minutes. Further drying under high vacuum for 5 hours provided the title compound as a free-flowing yellow resin.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with dichloromethane (20 mL×2)
  3. washThe resin was washed with diethyl ether (20 mL×3)
  4. customdried on a filter funnel
  5. customattached to a water aspirator for 30 minutes
  6. customFurther drying under high vacuum for 5 hours

Sources & evidence

ORD record
ord-32cc271ca66440ff93b6a68b88d2129d
Source dataset
uspto-grants-2003_03
Patent number
US06531485B2

Reaction notes

Loading…