Water → HCID 66975855, compound

HRID 1022812Notes

Reaction equation

HRID 1022812 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][C@H:4]1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1.C(N(CC)CC)C.C([O:35][CH2:36][C:37](Cl)=[O:38])(=O)C.O>C1COCC1>[Cl:24][C:19]1[CH:18]=[C:17]([C@H:4]2[C@H:3]([CH2:2][NH:1][C:36](=[O:35])[CH2:37][OH:38])[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 66976428HCID 66976428, compound

Product 1

HCID 66975855HCID 66975855, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6R,7R)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (170 mg) and triethylamine (0.126 mL) in THF (4.0 ml) was added acetoxyacetyl chloride (93 mg), and the mixture was stirred at room temperature overnight. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue in methanol (4.0 mL) was added potassium carbonate (273 mg), and the mixture was stirred at room temperature for 3 hr. The reaction solution was concentrated under reduced pressure, the residue was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (183 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionTo a solution of the obtained residue in methanol (4.0 mL) was added potassium carbonate (273 mg)
  6. stirringthe mixture was stirred at room temperature for 3 hr
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. additionthe residue was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe extract was washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-de0c093bb56c44a7b1d2fac423dda0d3
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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