Triethylamine → HCID 56622760, compound

HRID 2290430Notes

Reaction equation

HRID 2290430 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][CH2:16][C:17](=[O:26])[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1>C(#N)C>[CH2:8]([O:15][CH2:16][C:17](=[O:26])[C:18](=[N+:36]=[N-:37])[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 12035485Butanoic acid, 3-oxo-4-(phenylmethoxy)-, 1,1-dimethylethyl ester

Product 1

HCID 56622760HCID 56622760, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

5,54 ml (40 mmols--2 equivalents) of triethylamine was added dropwise to a solution, cooled to 0° C., of 5,29 g (20 mmols) of tert.-butyl 4-benzyloxyacetoacetate and 4,34 g. (22 mmols) of 4-toluenesulphonyl azide in 40 ml of anhydrons acetonitrile. The mixture was stirred for 30 minutes at 0° C., treated with 8 g of Celite and evaporated in vacuo. Chromatography of the residue on 100 g of silica gel (toluene:ethyl acetate 95:5) yielded 3,98 g of the title compound as colorless crystals, melting point: 68° C., RF : 0,31 (toluene:ethyl acetate 95:5).

Workup

  1. additiontreated with 8 g of Celite
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-c153892964994aebb30cbca8461e804c
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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