Methanesulfonamide → HCID 86598906, compound

HRID 456754Notes

Reaction equation

HRID 456754 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[C:21]#[N:22])=[O:15])[C@H:12]2[CH2:23][C@@H:9]1[C@H:10]([O:24][CH2:25][C:26](O)=[O:27])[CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30]([NH2:33])(=[O:32])=[O:31].N12CCCN=C1CCCCC2>CN(C)C=O>[C:21]([C@@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14]([C@@H:13]1[C@H:12]2[CH2:23][C@H:9]([C@H:10]([O:24][CH2:25][C:26]([NH:33][S:30]([CH3:29])(=[O:32])=[O:31])=[O:27])[CH2:11]2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:15])#[N:22]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69134660HCID 69134660, compound

Product 1

HCID 86598906HCID 86598906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [((1R,3S,4S,6R)-2-(tert-butoxycarbonyl)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-2-azabicyclo[2.2.1]hept-6-yl)oxy]acetic acid obtained in Example 15-2 (195 mg) in dimethylformamide (2.5 mL), was added 1,1′-carbonyldiimodazole (165 mg). The mixture was stirred at room temperature. After 30 minutes, methanesulfonamide (66 mg) and 1,8-diazabicyclo[5,4,0]undec-7-ene (106 mg) were added, and the resulting mixture was stirred at room temperature for 12 hrs.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 12 hrs

Sources & evidence

ORD record
ord-275626ea37ee4fc086300b239bbd030c
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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