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Hydrochloric Acid → Tert-butyl 7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-6-oxo-1,4-oxazepane-4-carboxylate

HRID 1022828
Notes
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Reaction equation

HRID 1022828 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10].[CH2:26]=O.Cl>C(O)C.CS(C)=O.[Cl-].[Na+].O>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([CH2:26][OH:1])[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 66976649HCID 66976649, compound

Product 1

HCID 66976886Tert-butyl 7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-6-oxo-1,4-oxazepane-4-carboxylateYield 456.5%

Reagents, catalysts & solvents 3

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 702EthanolSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium hydroxide (40 mg) was dissolved in ethanol (1.25 ml), and the solution was diluted with DMSO (25 mL). To this solution were added tert-butyl 7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate (2.60 g) and paraformaldehyde (267 mg), and the mixture was stirred at room temperature for 30 min. The reaction solution was neutralized with 1 N hydrochloric acid, brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.27 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed twice with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a60eb57a36b403b8f0a817f4aac6a6e
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722662B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes