Tributyltin Chloride → HCID 22390179, compound

HRID 1072368Notes

Reaction equation

HRID 1072368 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([C:9]2[N:10]=[CH:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)=[O:8])[CH:4]=[C:3]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:2]=1.C([Sn](Cl)(CCCC)CCCC)CCC.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Sn].[OH:53][C@@H:54]([C@H:56]1[C:77](=[O:78])[N:58]2[C@@H:59]([C:64]([O:66][CH2:67][C:68]3[CH:73]=[CH:72][C:71]([N+:74]([O-:76])=[O:75])=[CH:70][CH:69]=3)=[O:65])[C:60](=O)[C@H:61]([CH3:62])[C@H:57]12)[CH3:55].[N:79]1[CH:84]=[C:83]([C:85]([C:87]2[N:88]=[CH:89][N:90]3[CH:94]=[C:93]([Sn:95]([CH2:104][CH2:105][CH2:106][CH3:107])([CH2:100][CH2:101][CH2:102][CH3:103])[CH2:96][CH2:97][CH2:98][CH3:99])[S:92][C:91]=23)=[O:86])[CH:82]=[C:81]([C:108]2[CH:109]=[N:110][CH:111]=[CH:112][CH:113]=2)[CH:80]=1>>[N:79]1[CH:84]=[C:83]([C:85]([C:87]2[N:88]=[CH:89][N:90]3[CH:94]=[C:93]([Sn:95]([CH2:104][CH2:105][CH2:106][CH3:107])([CH2:100][CH2:101][CH2:102][CH3:103])[CH2:96][CH2:97][CH2:98][CH3:99])[S:92][C:91]=23)=[O:86])[CH:82]=[C:81]([C:108]2[CH:109]=[N:110][CH:111]=[CH:112][CH:113]=2)[CH:80]=1.[OH:53][C@@H:54]([C@H:56]1[C:77](=[O:78])[N:58]2[C:59]([C:64]([O:66][CH2:67][C:68]3[CH:69]=[CH:70][C:71]([N+:74]([O-:76])=[O:75])=[CH:72][CH:73]=3)=[O:65])=[C:60]([C:15]3[S:14][C:13]4=[C:9]([C:7]([C:5]5[CH:4]=[C:3]([C:17]6[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=6)[CH:2]=[N:1][CH:6]=5)=[O:8])[N:10]=[CH:11][N:12]4[CH:16]=3)[C@H:61]([CH3:62])[C@H:57]12)[CH3:55]

Participants

8

Reactant 6

HCID 15096Tributyltin ChlorideHCID 5352426Tin atomHCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 22390179HCID 22390179, compoundHCID 22390221HCID 22390221, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 2

HCID 22390179HCID 22390179, compoundHCID 91540949HCID 91540949, compound

Procedure

7-([3,3′]Bipyridinyl-5-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole was synthesized in substantially the same manner as in step c) of Synthesis Example 1, except that 263 mg of 7-([3,3′]bipyridinyl-5-yl)carbonylimidazo[5,1-b]thiazole, 0.316 ml of tri-n-butylstannyl chloride, and 1.72 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution were used as the starting compounds and, due to the unstable nature of the tin compound, the purification by column chromatography on silica gel was not carried out. 4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-([3,3′]bipyridinyl-5-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (80 mg) was prepared in substantially the same manner as in step a) of Example 1, except that 270 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 7-([3,3′]bipyridinyl-5-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.

Workup

  1. customof Synthesis Example 1
  2. customthe purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-2ac79c25174d4bcd8a6e6ab8e7ee2907
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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