Hydrochloric Acid → HCID 59361438, compound

HRID 888849Notes

Reaction equation

HRID 888849 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]2[CH:14]2[CH:21]3[CH2:22][C:17]4([C:24]([O:26]C)=[O:25])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)=[CH:4][CH:3]=1.O.[Na].Cl>O1CCCC1CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:10]([CH3:11])([CH3:12])[C:9](=[O:13])[N:8]2[CH:14]2[CH:21]3[CH2:22][C:17]4([C:24]([OH:26])=[O:25])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67303435HCID 67303435, compoundHCID 71353970Sodium monohydrate

Product 1

HCID 59361438HCID 59361438, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Conditions

Temperature
80 °C

Procedure

A solution of methyl 4-[2-(4-fluorobenzyl)-3,3-dimethyl-4-oxo-1,2-diazetidin-1-yl]adamantane-1-carboxylate (40.0 mg, 0.100 mmol) in tetrahydrofuran-methanol (1:1, 1 mL) was added with 2M aqueous solution of sodium hydrate (1 mL) at room temperature, and the resultant was stirred at 80° C. for 30 minutes. The reaction solution was neutralized with 4M hydrochloric acid, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=1:2), and the title compound (24.5 mg, 63.4%) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-edc8a811b72c47c6892e65fcb0e7a85c
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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