Methyl chloroglyoxylate → HCID 58032534, compound

HRID 405027Notes

Reaction equation

HRID 405027 reaction equation
CO[C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([C:34]([O:36]C(C)(C)C)=[O:35])[NH:18][C:19]([C:21]3[CH:22]=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)[CH:24]=[CH:25][CH:26]=3)=[O:20])=[CH:12][C:11]=2[F:41])[N:6]=1)=[O:4].C(OC(=O)[CH:48]([NH:61][C:62]([C:64]1[CH:65]=[C:66](C2C=CC(C)=CC=2)C=CC=1)=O)[CH2:49]C1C=CC(C(O)=NO)=C(F)C=1)(C)(C)C.COC(C(Cl)=O)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[F:41][C:11]1[CH:12]=[C:13]([CH2:16][CH:17]([NH:18][C:19]([C:21]2[CH:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[CH:24]=[CH:25][CH:26]=2)=[O:20])[C:34]([OH:36])=[O:35])[CH:14]=[CH:15][C:10]=1[C:7]1[N:6]=[C:5]([C:3]([N:61]2[CH2:48][CH2:49][CH:65]([CH3:66])[CH2:64][CH2:62]2)=[O:4])[O:9][N:8]=1

Participants

7

Reactant 4

HCID 79846Methyl chloroglyoxylateHCID 516892Sodium BicarbonateHCID 66631055HCID 66631055, compoundHCID 178423745HCID 178423745, compound

Product 1

HCID 58032534HCID 58032534, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

3-(4-{2-tert-Butoxycarbonyl-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-ethyl}-2-fluoro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid methyl ester. A mixture of 3-[3-fluoro-4-(hydroxy-hydroxyimino-methyl)-phenyl]-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-propionic acid tert-butyl ester (10 g, 0.02 mol) and methyl(chlorocarbonyl)formate (5 g, 0.04 mol), and pyridine (1 mL) in toluene (150 mL) was refluxed overnight. TLC showed the reaction was completed. An aqueous NaHCO3 solution (80 mL) was added to the reaction mixture, the layers were separated, and the aqueous portion was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×30 mL), dried over anhydrous sodium sulfate, filtered, concentrated, and purified by chromatography and recrystallization to give the title compound (7 g, 64% yield) as a white solid.

Workup

  1. temperaturewas refluxed overnight
  2. customthe layers were separated
  3. extractionthe aqueous portion was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with brine (2×30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography and recrystallization

Sources & evidence

ORD record
ord-ae14a9b15cb14f09b61c8565b02cb11e
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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