Water → 2-Aminocarbonyloxymethyl-6-methyl-4-(3-nitrophenyl)-3-ethoxycarbonyl-5-(beta-ethoxyethoxy)carbonyl-1,4-dihydropyridine

HRID 1995439Notes

Reaction equation

HRID 1995439 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]([CH3:31])=[C:6]([C:23]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH3:30])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].ClS([N:36]=[C:37]=[O:38])(=O)=O.O.C(OC(C)C)(C)C.CCCCCC>C1C=CC=CC=1>[NH2:36][C:37]([O:1][CH2:2][C:3]1[NH:4][C:5]([CH3:31])=[C:6]([C:23]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH3:30])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 130921522-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylateHCID 21881879Diisopropylether hexane

Product 1

HCID 130921162-Aminocarbonyloxymethyl-6-methyl-4-(3-nitrophenyl)-3-ethoxycarbonyl-5-(beta-ethoxyethoxy)carbonyl-1,4-dihydropyridineYield 62.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Hydroxymethyl-6-methyl-4-(3-nitrophenyl)-3-ethoxycarbonyl-5-(β-ethoxyethoxy)carbonyl-1,4-dihydropyridine (420 mg) was dissolved in benzene (20 ml), chlorosulfonyl isocyanate (0.2 ml) was added thereto, and the mixture was reacted under stirring at room temperature for 30 minutes. Water (10 ml) was added to the reaction mixture under cooling, and the mixture was stirred at room temperature for 30 minutes for hydrolysis. The reaction mixture thus obtained was extracted with ethyl acetate, and the extracted solution was washed with water, dried and then concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether/hexane, whereupon crystals (290 mg, yield: 62.6%) were obtained.

Workup

  1. customthe mixture was reacted
  2. temperatureunder cooling
  3. stirringthe mixture was stirred at room temperature for 30 minutes for hydrolysis
  4. customThe reaction mixture thus obtained
  5. extractionwas extracted with ethyl acetate
  6. washthe extracted solution was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02c72069074045b18b498c1608cf0e2b
Source dataset
uspto-grants-1983_09
Patent number
US04404378

Reaction notes

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