Aniline → HCID 178428779, compound

HRID 1603460Notes

Reaction equation

HRID 1603460 reaction equation
NC1C=CC=CC=1.C(OC([O:14][C@@H:15]([C@H:17]1[C:32](=[O:33])[N:19]2[C:20]([C:26]([O:28]CC=C)=[O:27])=[C:21]([CH2:24]O)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16])=O)C=C.C(OC([N:40]([CH2:45][C:46]1[S:50][C:49]2=[CH:51][N:52]=[CH:53][N:48]2[C:47]=1[CH3:54])[S:41]([NH2:44])(=[O:43])=[O:42])=O)C=C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:14][C@@H:15]([C@H:17]1[C:32](=[O:33])[N:19]2[C:20]([C:26]([O-:28])=[O:27])=[C:21]([CH2:24][N:52]3[CH:51]=[C:49]4[S:50][C:46]([CH2:45][NH:40][S:41]([NH2:44])(=[O:42])=[O:43])=[C:47]([CH3:54])[N+:48]4=[CH:53]3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16]

Participants

6

Reactant 3

HCID 6115AnilineHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 196051242-(N-allyloxycarbonyl-N-aminosulfonylamino)methyl-3-methylimidazo[5,1-b]thiazole

Product 1

HCID 178428779HCID 178428779, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The same procedure as in Example 1 was repeated except that in a deprotective reaction, two catalysts, i.e., 23.4 mg of tris(dibenzylideneacetone)dipalladium and 59.1 mg of tetrakis(triphenylphosphine)palladium were used, 0.14 ml of aniline was used as a trapping agent, and 110.3 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 196 mg of 2-[N-allyloxycarbonyl-N-(aminosulfonyl)amino]methyl-3-methylimidazo[5,1-b]thiazole were used, thereby obtaining 14.2 mg of the title compound.

Sources & evidence

ORD record
ord-24b6f05e75fe408d9aeff3f4c5d6b50c
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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