Benzoic acid, 4-(azidosulfonyl)- → HCID 86629545, compound

HRID 1011608Notes

Reaction equation

HRID 1011608 reaction equation
C(C1C=CC(S([N:13]=[N+:14]=[N-])(=O)=O)=CC=1)(O)=O.[CH:16]1([C@@H:19]([NH:28][S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[CH2:20][C:21](=[O:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]1>CC#N.CCOC(C)=O>[CH:16]1([C@@H:19]([NH:28][S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[CH2:20][C:21](=[O:27])[C:22](=[N+:13]=[N-:14])[C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 86999Benzoic acid, 4-(azidosulfonyl)-HCID 67314184HCID 67314184, compound

Product 1

HCID 86629545HCID 86629545, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Carboxybenzenesulfonyl azide (28) (8.79 g, 38.7 mmol) was added to a solution of (5S)-methyl 5-cyclopropyl-5-[(R)-1,1-dimethylethylsulfinamido]-3-oxopentanoate (27) (10.2 g, 35.2 mmol) in CH3CN (230 mL) and the resulting solution was stirred at rt for 5 h. The resulting solution was diluted with EtOAc (200 mL) and washed with sat. brine (100 mL). The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to give (5S)-methyl 5-cyclopropyl-2-diazo-5-[(R)-1,1-dimethylethylsulfinamido]-3-oxopentanoate (29). Retention time (min)=1.634 method [1], MS (m/z) 316.2 (M+H)+.

Workup

  1. washwashed with sat. brine (100 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-84026947a08547c892ff95851b6731f5
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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