Acetic Acid → HCID 20812832, compound

HRID 1372441Notes

Reaction equation

HRID 1372441 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O: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:49]=[N+:50]=[N-:51])(=O)=O)(C)C.C(O)(=O)C>C1COCC1>[CH3:20][O:19][C:17](=[O:18])[CH:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])=[CH:15][CH:14]=1)[N:49]=[N+:50]=[N-:51]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22382479Methyl (4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acetate

Product 1

HCID 20812832HCID 20812832, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-(N-BOC-aminomethyl)phenylacetate (9.34 g; 0.033 mol) in THF (100 mL) was stirred under argon at −78° C. and potassium bis(trimethylsilyl)amide (16.7 g, 0.084 mol) in THF (50 mL) was added. After stirring for 30 minutes, 2,4,6-triisopropylbenzene-sulfonyl azide (31.1 g, 0.101 mol) was added as a solid. After 5 minutes, acetic acid (10 mL, 0.175 mol) was added and the reaction warmed to room temperature. The reaction mixture was then partitioned between ethyl acetate (500 mL) and water (500 mL), separated and the organic layer dried (MgSO4). Evaporation of the solvent and purification of the residue by silica gel chromatography afforded the azide (7.1 g, 67%).

Workup

  1. waitAfter 5 minutes
  2. customThe reaction mixture was then partitioned between ethyl acetate (500 mL) and water (500 mL)
  3. customseparated
  4. dry with materialthe organic layer dried (MgSO4)
  5. customEvaporation of the solvent and purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-2eec43a9bb71480da97807baf8b9da51
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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