Dimethylformamide → HCID 57013107, compound

HRID 582481Notes

Reaction equation

HRID 582481 reaction equation
ClC1C=CC(S(O[CH2:12][C@@H:13]2[O:19][C@@H:18]3[N:15]([C:16](=[O:20])[CH2:17]3)[CH2:14]2)(=O)=O)=CC=1.[N-:21]=[N+:22]=[N-:23].[Na+].CN(C=O)C>C(OCC)(=O)C>[N:21]([CH2:12][C@H:13]1[O:19][C@@H:18]2[N:15]([C:16](=[O:20])[CH2:17]2)[CH2:14]1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 21310371HCID 21310371, compound

Product 1

HCID 57013107HCID 57013107, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (3R,5S)-3-(4-chlorobenzenesulfonyl)oxymethyl-4-oxa-1-azabicyclo [3,2,0] heptan-7-one (400 mg, 1.26 mmol), sodium azide (212 mg, 3.8 mmol) and DMF (5 ml) was stirred at 65° C. for 2 hrs. The resulting mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as eluent and 210 mg of (3S,5S)-3-azidomethyl-4-oxa-1-azabicyclo [3,2,0] heptan-7-one was obtained.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c2a163a56eaa4dabb52a4f14d56c4d75
Source dataset
uspto-grants-1999_07
Patent number
US05925633

Reaction notes

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