Triethylamine → Methyl 2-diazo-7-methoxy-3-oxoheptanoate

HRID 1184217Notes

Reaction equation

HRID 1184217 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10].C(NC1C=CC(S([N:27]=[N+:28]=[N-])(=O)=O)=CC=1)(=O)C.C(N(CC)CC)C>C(#N)C>[N+:27](=[C:8]([C:7](=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:9]([O:11][CH3:12])=[O:10])=[N-:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 58355424Methyl 7-methoxy-3-oxoheptanoate

Product 1

HCID 76731428Methyl 2-diazo-7-methoxy-3-oxoheptanoateYield 121.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution (100 ml) of methyl 7-methoxy-3-oxoheptanoate (5.00 g) and 4-(acetylamino)benzenesulfonyl azide (7.02 g) in acetonitrile was added triethylamine (11.1 ml) and the mixture was stirred at room temperature for 2 days. Insoluble material was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was suspended in diethyl ether and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure to give the object product (6.93 g).

Workup

  1. filtrationInsoluble material was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3365844a40384192ac236ec37af721e7
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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