Water → HCID 57683627, compound

HRID 604862Notes

Reaction equation

HRID 604862 reaction equation
[OH:1][CH:2]([CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[N+:23]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28](F)[CH:27]=1)([O-:25])=[O:24].[H-].[Na+].O>CN(C=O)C.CCOC(C)=O.[NH4+].[Cl-]>[F:32][C:30]1[CH:29]=[C:28]([CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:31]=1)[O:1][CH:2]([CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 752721,3-Difluoro-5-nitrobenzeneHCID 22485464tert-butyl N-(3-{[(tert-butoxy)carbonyl](methyl)amino}-2-hydroxypropyl)-N-methylcarbamate

Product 1

HCID 57683627HCID 57683627, compoundYield 47.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To 15.0 g (47.1 mmol) of di-tert-butyl 2-hydroxypropane-1,3-diylbis(methylcarbamate) and 11.9 g (75 mmol) of 1-nitro-3,5-difluorobenzene in 100 ml DMF under N2 at 0° C. was added 2.4 g (60 mmol) of NaH in portions. The resultant mixture was stirred at 0° C. for 30 min after which approximately 1 mL of H2O was added slowly. The reaction mixture was diluted with 200 mL EtOAc and 200 mL saturated NH4Cl. The layers were separated and the organic layer was washed with 200 mL of saturated NH4Cl. The organic layer was dried and concentrated. Then the residue was purified by column chromatography over silica gel (EtOAc:Hex=1:6) to give 10.3 g (45%) of di-tert-butyl 2-(3-fluoro-5-nitrophenoxy)propane-1,3-diylbis(methylcarbamate).

Workup

  1. additionwas added slowly
  2. customThe layers were separated
  3. washthe organic layer was washed with 200 mL of saturated NH4Cl
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThen the residue was purified by column chromatography over silica gel (EtOAc:Hex=1:6)

Sources & evidence

ORD record
ord-1895467349d84228bb4cf3f4612262a5
Source dataset
uspto-grants-2011_03
Patent number
US07910743B2

Reaction notes

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