Water → HCID 66976471, compound

HRID 1022784Notes

Reaction equation

HRID 1022784 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.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:34].O>C1COCC1>[Cl:24][C:19]1[CH:18]=[C:17]([C@H:4]2[C@@H:3]([CH2:2][NH:1][C:33]([O:35][C:36]3[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=3)=[O:34])[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 821294-Nitrophenyl chloroformateHCID 66975545HCID 66975545, compound

Product 1

HCID 66976471HCID 66976471, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6R,7S)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) and triethylamine (0.149 mL) in THF (4.0 mL) was added 4-nitrophenyl chloroformate (129 mg) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. 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. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (99 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 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-3c730ce5891647a49f704c3121bac9a6
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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