Trimethylsilyldiazomethane → HCID 67043761, compound

HRID 473034Notes

Reaction equation

HRID 473034 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24]3)[C:8]2([NH:14][S:15]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])(=[O:17])=[O:16])[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:35]>C(Cl)Cl.CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]3)[C:8]2([NH:14][S:15]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:21])[CH3:22])(=[O:17])=[O:16])[C:11]([O:13][CH3:35])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67043853HCID 67043853, compound

Product 1

HCID 67043761HCID 67043761, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6′-bromo-1-(tert-butoxycarbonyl)-1′-(2-(trimethylsilyl)ethylsulfonamido)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1′-carboxylic acid, obtained as described above, and TMSCHN2 (2.0 Min hexane, 1 mL) in CH2Cl2 (6 mL) and MeOH (3 mL) was stirred at room temperature for 19 h. After the solvent was evaporated under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.3263 g (72% in three steps) of 1-tert-butyl 1′-methyl 6′-bromo-1′-(2-(trimethylsilyl)ethylsulfonamido)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1,1′-dicarboxylate as foam. LC-MS tR=2.20 min in 3 min chromatography, m/z 575, 577 (MH+), 547, 549 (MH+-28), 519, 521 (MH+-56).

Workup

  1. customobtained
  2. customAfter the solvent was evaporated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-bd04e8cdeb114ff9820de327c4715af2
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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