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Monobasic potassium phosphate → (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

HRID 1022617
Notes
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Reaction equation

HRID 1022617 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[CH:23]=[O:24])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[K+]>CC(=CC)C.C(O)(C)(C)C.C1COCC1.O.C(OCC)(=O)C>[C:19]([O:18][C:16]([N:12]1[CH2:11][C@@H:10]([C:23]([OH:26])=[O:24])[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13]1)=[O:17])([CH3:20])([CH3:21])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86663853tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acidYield 92%

Reagents, catalysts & solvents 5

HCID 962
Water
Solvent
HCID 6386tert-ButanolSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent
HCID 105532-Methyl-2-buteneSolvent

Procedure

To a mixed solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (7.3 g) in 2-methyl-2-butene (45 mL), tert-butanol (100 ml) and THF (100 ml) was added dropwise a solution of sodium chlorite (10.58 g) and potassium dihydrogenphosphate (16.38 g) in water (160 ml) under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (7.0 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. washThe diluted solution was washed with distilled water and 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-a2154aebb6c4485a92c9525bcfe0c84d
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