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

HRID 1022806Notes

Reaction equation

HRID 1022806 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].I([O-])(=O)(=O)=[O:26].[Na+].C(OCC)(=O)C.O>C(#N)C.[Ru](Cl)(Cl)Cl>[C:21]([O:20][C:18]([N:11]1[CH2:10][C@@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C@H:15]([C:16]([OH:26])=[O:17])[O:14][CH2:13][CH2:12]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 66975324tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976870(6R,7R)-4-(tert-butoxycarbonyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-7-carboxylic acidYield 10%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixed solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (3.0 g) and sodium periodate (3.41 g) in acetonitrile (16 mL)/ethyl acetate (16 mL)/water (24 mL) was added ruthenium (III) chloride (17 mg), and the mixture was stirred at room temperature for 10 min. The solid was filtered off through celite, and the filtrate was concentrated. The residue was crystallized from ethyl acetate to give the title compound (311 mg) as a colorless amorphous powder.

Workup

  1. filtrationThe solid was filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-644a2a9344b54ffca1346abd0c67eccd
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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