Ammonium Hydroxide → HCID 13457209, compound

HRID 2290320Notes

Reaction equation

HRID 2290320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]2[S:23][CH:24]=[C:25]([C:27](OCC)=[O:28])[N:26]=2)=[C:9]1[C:32]([O:34][CH2:35][CH3:36])=[O:33].[OH-].[NH4+:38]>O1CCOCC1>[C:27]([C:25]1[N:26]=[C:22]([CH2:21][O:20][CH2:19][C:10]2[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[S:23][CH:24]=1)(=[O:28])[NH2:38]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 13457207HCID 13457207, compound

Product 1

HCID 13457209HCID 13457209, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-ethoxycarbonylthiazole (0.54 g), dioxane (20 ml) and 0.880 aqueous ammonium hydroxide solution (20 ml) was stirred at room temperature for 43 hours and then evaporated. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried (Na2SO4) and evaporated. The residual oil was purified by chromatography on silica (t.l.c. grade, 10 g) using dichloromethane plus 0-3% v/v methanol as eluant. Appropriate fractions were combined and evaporated and the residual oil triturated with diethyl ether. The resulting solid was collected, washed with diethyl ether and dried to give the title compound (0.30 g) as a monohydrate, m.p. 160°-164° C. decomp.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residual oil was purified by chromatography on silica (t.l.c. grade, 10 g)
  7. customevaporated
  8. customthe residual oil triturated with diethyl ether
  9. customThe resulting solid was collected
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-6f4d37845d9a417085b7ddea47fa93e0
Source dataset
uspto-grants-1986_10
Patent number
US04616024

Reaction notes

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