HCID 54429135, compound → HCID 22718738, compound

HRID 1582639Notes

Reaction equation

HRID 1582639 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([N:21]=[N+]=[N-])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]=1[F:20]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[NH:21][C:11]2[C:6]([CH:5]=1)=[C:7]([F:20])[C:8]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][CH:10]=2)=[O:24]

Participants

3

Reactant 1

HCID 54429135HCID 54429135, compound

Product 1

HCID 22718738HCID 22718738, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of methyl-2-azido-3-(2-fluoro-3-benzyloxyphenyl)propenoate (16.7 g) in xylene (600 ml) was added dropwise with stirring to refluxino xylene (2.4 L) over 1 hour and then stirred for a further 20 minutes. The reaction mixture was concentrated in vacuo and purified by flash column chromatography, using a gradient of 0-100% ethyl acetate/iso-hexane as eluent to give the product as a yellow solid (12.93 g) 1H NMR (DMSO-d6) δ 3.85(s, 3H), 5.15(s, 2H), 7.05-7.45(m, 8H), 12.06(s, 1H); M/z(+) 300.4 (MH+)

Workup

  1. customover 1 hour
  2. stirringstirred for a further 20 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-6966961710c840ca9c0952d48bd8d59f
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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