p-Toluenesulfonyl azide → (4-Cyclopropanesulfonyl-phenyl) diazo acetic acid ethyl ester

HRID 524388Notes

Reaction equation

HRID 524388 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C1(C)C=CC(S([N:28]=[N+:29]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[N+:28]=[N-:29])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59331225Ethyl 2-(4-(cyclopropylsulfonyl)phenyl)acetate

Product 1

HCID 72281714(4-Cyclopropanesulfonyl-phenyl) diazo acetic acid ethyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-(4-cyclopropylsulfonylphenyl)acetate [obtained as described in WO2004/072031 (40 g, 149.07 mmol)] was dissolved in dry acetonitrile (745 mL) under argon atmosphere. To the above solution para toluene sulfonyl azide (32.33 g, 163.97 mmol) was added, followed by DBU (33.40 mL, 223.6 mmol) in dropwise manner, and stirred for 30 min. Reaction mixture was poured in ice cold water (500 mL), solid obtained was filtered through buchner funnel and dried under vaccum which yielded ethyl 2-(4-cyclopropylsulfonylphenyl)-2-diazo-acetate (40 g).

Workup

  1. customReaction mixture
  2. customsolid obtained
  3. filtrationwas filtered through buchner funnel
  4. customdried under vaccum which

Sources & evidence

ORD record
ord-c391536ab416455e8640580b829a854e
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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