Ethyl bromoacetate → HCID 66625110, compound

HRID 417373Notes

Reaction equation

HRID 417373 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)C(C)C)(C)C.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(Cl)Cl.CCOC(C)=O>[C:4]([O:3][C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13][CH:14]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 66625110HCID 66625110, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step A To a solution of N-Boc-1,4-phenylene diamine (Aldrich, 1.00 g, 4.82 mmol) in CH2Cl2 (12 ml) were added N,N-diisopropylethylamine (1.26 g, 9.76 mmol) and ethyl bromoacetate (Aldrich, 813 mg, 4.87 mmol). The mixture was allowed to stir at rt overnight and then taken up in EtOAc (300 ml) and washed with sat. aqueous Na2CO3, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give ethyl 2-(4-(tert-butoxycarbonylamino)phenylamino)acetate as a light brown oil (1.33 g, 94%).

Workup

  1. washwashed with sat. aqueous Na2CO3, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bc3a7a169a64e9a85d92dcb2646ffeb
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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