allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate → (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(2-(formylamino)methyl-3-methylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1603452Notes

Reaction equation

HRID 1603452 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21]CC=C)=[O:20])=[C:14]([CH2:17]O)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=O)C=C.[CH:27]([NH:29][CH2:30][C:31]1[S:35][C:34]2=[CH:36][N:37]=[CH:38][N:33]2[C:32]=1[CH3:39])=[O:28]>>[OH:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O-:21])=[O:20])=[C:14]([CH2:17][N:37]3[CH:36]=[C:34]4[S:35][C:31]([CH2:30][NH:29][CH:27]=[O:28])=[C:32]([CH3:39])[N+:33]4=[CH:38]3)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9]

Participants

3

Reactant 2

HCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 196050132-(Formylamino)methyl-3-methylimidazo[5,1-b]thiazole

Product 1

HCID 178428685(1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(2-(formylamino)methyl-3-methylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylateYield 3.8%

Procedure

The same procedure as in Example 1 was repeated except that 91.3 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 100 mg of 2-(formylamino)methyl-3-methylimidazo[5,1-b]thiazole were used, thereby obtaining 4 mg of the title compound.

Sources & evidence

ORD record
ord-4a404029b9bd4005ba11a8498e7a5cdf
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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