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Dimethylformamide → 2-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid

HRID 1270405
Notes
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Reaction equation

HRID 1270405 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Br:10][C:11]1[CH:22]=[CH:21][C:14]2[C:15](=[O:20])[O:16]C(=O)[NH:18][C:13]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].C[N:32](C=O)C>>[NH2:32][CH:2]([NH:18][C:13]1[CH:12]=[C:11]([Br:10])[CH:22]=[CH:21][C:14]=1[C:15]([OH:16])=[O:20])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 115215774-Bromoisatoic anhydride

Product 1

HCID 184493622-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid

Procedure

tert-Butyl bromoacetate (1.34 mL, 9.1 mmol) was added to a solution of 7-bromo-2H-3,1-benzoxazine-2,4(1H)-dione from Step B (2 g, 8.26 mmol) and potassium carbonate (1.3 mg, 9.1 mmol) in DMF (20 mL) and stirred at ambient temperature for 4 h. 1 N NaOH (15 mL) was then added to the reaction and after 1 h, the mixture was partitioned between 0.5 N HCl and EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound in sufficient purity for use in the next step. MS: m/z=275 (M+1-tert-butyl).

Workup

  1. customthe mixture was partitioned between 0.5 N HCl and EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-87b09aaf625042bd801dbc50afd3aedd
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07202251B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes