Sodium Bicarbonate → (4-tert-Butoxycarbonylamino-2-nitro-phenylamino)-acetic acid tert-butyl ester

HRID 15574

Reaction equation

HRID 15574 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].C([O-])(O)=O.[Na+].[C:16]([O:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[CH:27][C:26](F)=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)([CH3:19])([CH3:18])[CH3:17]>CS(C)=O>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:21]([O:20][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:33])=[CH:24][C:25]=1[N+:30]([O-:32])=[O:31])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 11118665Tert-butyl 4-fluoro-3-nitrophenylcarbamate

Product 1

HCID 67201113(4-tert-Butoxycarbonylamino-2-nitro-phenylamino)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Glycine tert-butyl ester hydrochloride (4.1 g, 29.4 mmol) and NaHCO3 (5.1 g, 61.0 mmol) were added to a solution of (4-fluoro-3-nitro-phenyl)-carbamic acid tert-butyl ester (5.2 g, 20.3 mmol) in DMSO (16 mL). The reaction was heated to 65° C. for 5 hours, cooled to room temperature, and partitioned between H2O and EtOAc. The organic layer was washed several times with H2O and concentrated to afford the sub-title compound. MS calculated for C17H25N3O6+H: 368, observed: 368.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between H2O and EtOAc
  3. washThe organic layer was washed several times with H2O
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d34867f288344e0b81e93b133d1f1951
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Linked notes

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