Triethylamine → HCID 86024925, compound

HRID 1396386Notes

Reaction equation

HRID 1396386 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.C(NC1C=CC(S([N:33]=[N+:34]=[N-])(=O)=O)=CC=1)(=O)C.[O-][Mn](=O)(=O)=O.[K+]>C(#N)C.CCCCCC.C(OCC)(=O)C>[CH3:12][O:11][C:9](=[O:10])[C:8](=[N+:33]=[N-:34])[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 74591Dimethyl 3-oxoglutarateHCID 516875Potassium PermanganateHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 86024925HCID 86024925, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of dimethyl 3-oxopentanedioate (50.0 g, 287.1 mmol) and triethylamine (47.8 mL, 344.5 mmol) in acetonitrile (1.2 L) at 0° C. was added 4-acetamidobenzene sulfonyl azide (69.0 g, 287.1 mmol) portion wise. After addition was completed, the reaction mixture was stirred at room temperature for 1 h (silica TLC; ethyl acetate:hexane=1:4, Rf=0.3; showed KMnO4 activity). The reaction mixture was filtered, and the filtrate was concentrated to get a viscous mass, which was diluted with n-hexane (3 L). The unwanted solid byproduct was removed by filtration then filtrate was concentrated under reduced pressure to give 2-diazo-3-oxo-pentanedioic acid dimethyl ester (50.0 g, 87% crude yield) as a light yellow liquid, which was directly used for next step without further purification.

Workup

  1. additionAfter addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto get a viscous mass, which
  5. customThe unwanted solid byproduct was removed by filtration
  6. concentrationfiltrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1310c924cca42b792d249e5ac04fdac
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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