Water → HCID 140482358, compound

HRID 2214771Notes

Reaction equation

HRID 2214771 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([CH2:22][CH2:23][C:24]=2[SH:25])[C@@H:20]([NH:26][C:27](=[O:57])/[C:28](/[C:50]2[N:51]=[C:52]([NH2:56])[S:53][C:54]=2[Cl:55])=[N:29]\[O:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:19]3=[O:58])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:59]([O:63][C:64]([NH:66][CH2:67][CH2:68][S:69][CH2:70][C:71]1[CH:72]=[N:73][CH:74]=[CH:75][C:76]=1Cl)=[O:65])([CH3:62])([CH3:61])[CH3:60].O>CN(C)C=O>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([CH2:22][CH2:23][C:24]=2[S:25][C:76]2[CH:75]=[CH:74][N:73]=[CH:72][C:71]=2[CH2:70][S:69][CH2:68][CH2:67][NH:66][C:64]([O:63][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:65])[C@@H:20]([NH:26][C:27](=[O:57])/[C:28](/[C:50]2[N:51]=[C:52]([NH2:56])[S:53][C:54]=2[Cl:55])=[N:29]\[O:30][C:31]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:19]3=[O:58])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10804366HCID 10804366, compoundHCID 140482360HCID 140482360, compound

Product 1

HCID 140482358HCID 140482358, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino]-acetamido]-3-mercapto-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (3.0 g, 0.0036 mol) in dimethylformamide (30 mL) was added 3-(N-tert-butoxycarbonylaminoethylthiomethyl)-4-chloropyridine (1.3 g, 0.0043 mol) at room temperature. After stirring overnight, the reaction mixture was treated with water (200 mL), and the solid that formed was filtered and dried to afford the crude title compound (2.9 g).

Workup

  1. customthe solid that formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-63402384a2a04e5bb26cbb1f341e651d
Source dataset
uspto-grants-2006_09
Patent number
US07109190B2

Reaction notes

Loading…