Hydrochloric Acid → RS-93522

HRID 2074033Notes

Reaction equation

HRID 2074033 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:41])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH:34]3[CH2:38][O:37]C(C)(C)[O:35]3)=[CH:28][CH:27]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].Cl>CC(C)=O.O>[CH3:1][C:2]1[NH:3][C:4]([CH3:41])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH:34]([OH:35])[CH2:38][OH:37])=[CH:28][CH:27]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136325642,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridine

Product 1

HCID 128487RS-93522

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of 21 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridine in 150 mL of acetone and 50 mL of water is treated with 10 mL of hydrochloric acid and the mixture heated at reflux for 6 h. Water (500 mL) is added and the mixture was extracted with ether. The ether layer is dried over Na2SO4 and evaporated to an oil which is purified by medium pressure chromatography on silica gel (90% ethyl acetate-hexane) to give 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,3-dihydroxypropoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine, m.p. 117-118° C., [α]D =-33.5°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 6 h
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe ether layer is dried over Na2SO4
  5. customevaporated to an oil which
  6. customis purified by medium pressure chromatography on silica gel (90% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7c911318d64e4639acc0b07ef552f76f
Source dataset
uspto-grants-1990_04
Patent number
US04920225

Reaction notes

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