Methanesulfonyl chloride → HCID 86599409, compound

HRID 1392156Notes

Reaction equation

HRID 1392156 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C@@:7]23[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]2[C:10](=[O:16])[N:9]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[C:8]3=[O:25])=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl.CCN(C(C)C)C(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]23[CH2:14][C@@H:13]([O:15][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:12][N:11]2[C:10](=[O:16])[N:9]([C:17]2[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)[C:8]3=[O:25])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59124109HCID 59124109, compound

Product 1

HCID 86599409HCID 86599409, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of (5S,7R)-5-(4-bromobenzyl)-3-(3,5-dichloro-phenyl)-7-hydroxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.81 g) in CH2Cl2 (5 mL) and DIEA (0.50 mL) at 0° C. was added methanesulfonyl chloride (0.19 mL). After 1 hour at 0° C., the mixture was diluted with CH2Cl2, washed with satd. NaHCO3 and brine, dried (Na2SO4) and concentrated to give (5S, 7R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-7-methylsulfonyloxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione. MS (m/z) 494 (MH+). (2) To a solution of the compound obtained above in DMF (4 mL) at 75° C. was added sodium azide (0.54 g). After heating for 2 hours the mixture was diluted with Et2O and water. The organic solution was collected, washed with water and brine, dried (Na2SO4), filtered and concentrated. Purification by chromatography (silica gel: 2% methanol/CH2Cl2, Chromatotron) afforded the titled compound (0.82 g). MS (m/z) 494 (MH+), mp 58.9° C.

Workup

  1. washwashed with satd
  2. dry with materialNaHCO3 and brine, dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ff90b6309fc7411fb49af04d17ea1c6b
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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