Hydrochloric Acid → HCID 178493270, compound

HRID 630416Notes

Reaction equation

HRID 630416 reaction equation
[OH:1][C:2]([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22](/[CH:27]=[CH:28]/[O:29]C)=[CH:21][C:20]=2[Cl:31])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4].Cl>>[OH:1][C:2]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][CH:28]=[O:29])=[CH:21][C:20]=2[Cl:31])=[O:17])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178494774HCID 178494774, compound2×

Product 1

HCID 178493270HCID 178493270, compoundYield 90%

Conditions

Temperature
65 °C

Procedure

To a solution of trans-4-[[3-({2-chloro-5-methoxy-4-[(E)-2-methoxyvinyl]phenyl}amino)-3-oxopropyl](methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 122; 0.36 g, 0.17 mmol) in anhydride tetrahydrofurane (0.5 mL) was added dropwise hydrochloric acid 2M (0.34 mL, 0.7 mmol). The mixture was stirred at 65° C. for 5 hours and a half. A mixture of water/ice was poured into the reaction and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was removed under reduced pressure. The crude obtained was purified by column chromatography with silica gel, eluting with methylen chloride/methanol (95:5) to give the title compound as an oil (90%).

Workup

  1. additionwas poured into the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe crude obtained
  7. customwas purified by column chromatography with silica gel
  8. washeluting with methylen chloride/methanol (95:5)

Sources & evidence

ORD record
ord-b11f0fd66364414bb8cae91fd4648a1e
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…