1,1'-Carbonyldiimidazole → ethyl 2-amino-2-(((2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoyl)oxy)imino)acetate

HRID 1427272Notes

Reaction equation

HRID 1427272 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)([CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:43][CH2:44][O:45][C:46](/[C:48](/[NH2:51])=[N:49]/O)=[O:47]>C(Cl)Cl.CCOC(C)=O>[NH2:51][C:48](=[N:49][O:20][C:19](=[O:21])[C:18]([N:13]1[C:14]2[C:10](=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[N:12]1)([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:22][CH3:23])[C:46]([O:45][CH2:44][CH3:43])=[O:47]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 9614369Ethyl 2-oximinooxamateHCID 705627322-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid

Product 1

HCID 86705053ethyl 2-amino-2-(((2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoyl)oxy)imino)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid from Step A above (0.16 g, 0.37 mmol) in DCM (1.5 mL) was added 1,1′-carbonyldiimdazole (0.13 g, 0.78 mmol) to give a clear solution. The mixture was stirred for 7.5 hours at RT followed by addition of ethyl 2-oximinooxamate (0.13 g, 0.93 mmol). After stirring at RT overnight, the resulting mixture was diluted with EtOAc, washed with saturated NaHCO3 solution, water and brine. The organic layer was separated, and concentrated. The resulting crude product was re-dissolved in a mixture of acetonitrile and water and dried in a lyophilized to give the title compound as light yellow solid. LC/MS m/z=544.1[M+H]+.

Workup

  1. customto give a clear solution
  2. stirringAfter stirring at RT overnight
  3. washwashed with saturated NaHCO3 solution, water and brine
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. dissolutionThe resulting crude product was re-dissolved in a mixture of acetonitrile and water
  7. customdried in

Sources & evidence

ORD record
ord-fde9457fdff347458f64c222c775abed
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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