Water → HCID 66975556, compound

HRID 1022785Notes

Reaction equation

HRID 1022785 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][NH:17][C:18](OC3C=CC([N+]([O-])=O)=CC=3)=[O:19])[O:14][CH2:13][CH2:12][N:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:38][O:39][C:40](=[O:44])[CH2:41][NH:42][CH3:43].C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][NH:17][C:18](=[O:19])[N:42]([CH2:41][C:40]([O:39][CH3:38])=[O:44])[CH3:43])[O:14][CH2:13][CH2:12][N:11]([C:30]([O:32][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:31])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 66976471HCID 66976471, compound

Product 1

HCID 66975556HCID 66975556, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-({[(4-nitrophenoxy)carbonyl]amino}methyl)-1,4-oxazepane-4-carboxylate (94 mg) in THF (2.0 mL) were added sarcosine methyl ester hydrochloride (36 mg) and potassium carbonate (72 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. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (79 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. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0e6cc9d7d4bc4ee4bdb2616a97c1c6de
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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