Hydrochloric Acid → HCID 15005366, compound

HRID 1088660Notes

Reaction equation

HRID 1088660 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]CCC#N)=[O:15])=[C:12]([CH3:21])[NH:11][C:10]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[C:36]4[CH:35]=[CH:34][N:33]=[CH:32][C:31]=4[N:30]=[C:29]3[CH3:37])=[CH:24][CH:23]=2)=[C:9]1[C:38]([O:40][CH2:41][CH3:42])=[O:39].[OH-].[Na+].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:21])[NH:11][C:10]([C:22]2[CH:23]=[CH:24][C:25]([N:28]3[C:36]4[CH:35]=[CH:34][N:33]=[CH:32][C:31]=4[N:30]=[C:29]3[CH3:37])=[CH:26][CH:27]=2)=[C:9]1[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15005381HCID 15005381, compound

Product 1

HCID 15005366HCID 15005366, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the (-)-cyanoethyl ester of Example 8 (271 mg, 0.466 mmol) and aqueous sodium hydroxide (2.54 ml, 0.55M, 1.40 mmol) in dioxane (7.5 ml) was stirred at room temperature under nitrogen for 1 hour. Hydrochloric acid (1.40 ml, 1M, 1.40 mmol) was added dropwise, and the mixture was concentrated under reduced pressure. The resulting yellow solid was suspended in water, filtered off, and dried in vacuo, to give the title compound, (200 mg, 81%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. filtrationfiltered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-aac97ebcbfda4e4bbc3e185cd1d24e27
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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