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

HRID 2169030Notes

Reaction equation

HRID 2169030 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-8808dd58a1c442579e4ff1e8d3f30ae7
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

Loading…