Acetic Acid → HCID 22382628, compound

HRID 1372443Notes

Reaction equation

HRID 1372443 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][CH:12]=[O:13])[S:9][CH:10]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:43]=[N+:44]=[N-:45])(=O)=O)(C)C.C(O)(=O)C>C1COCC1>[N:43]([CH:5]([C:6]1[N:7]=[C:8]([NH:11][CH:12]=[O:13])[S:9][CH:10]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:14])=[N+:44]=[N-:45]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 688091Ethyl 2-formamidothiazol-4-acetateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 22382628HCID 22382628, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl[2-(N-formylamino)thiazol-4-yl]acetate (1 g, 0.0047 mol) in THF (10 mL) was stirred under argon at −78° C. and potassium bis(trimethylsilyl)amide (2.8 g, 0.014 mol) in THF (10 mL) was added. After stirring for 30 minutes, 2,4,6-triisopropylbenzenesulfonyl azide (3.6 g, 0.012 mol) was added as a solid in one portion. After 5 minutes, acetic acid (1.4 mL, 0.018 mol) was added and the mixture warmed to room temperature. The reaction mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), separated and the organic layer dried (MgSO4). Evaporation of the solvent and purification of the residue by silica gel chromotography afforded the azide (0.95 g, 80%).

Workup

  1. waitAfter 5 minutes
  2. customThe reaction mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customseparated
  4. dry with materialthe organic layer dried (MgSO4)
  5. customEvaporation of the solvent and purification of the residue by silica gel chromotography

Sources & evidence

ORD record
ord-996e0c8d0f31486fab264c1d106ab456
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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