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-(3-phenylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1603507Notes

Reaction equation

HRID 1603507 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.[C:27]1([C:33]2[N:34]3[CH:40]=[N:39][CH:38]=[C:35]3[S:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[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:39]3[CH:38]=[C:35]4[S:36][CH:37]=[C:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N+:34]4=[CH:40]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 234493013-Phenylimidazo[5,1-b]thiazole

Product 1

HCID 178462296(1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(3-phenylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylateYield 13.4%

Procedure

The same procedure as in Example 1 was repeated except that 104 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 86 mg of 3-phenylimidazo[5,1-b]thiazole were used, thereby obtaining 16.2 mg of the title compound.

Sources & evidence

ORD record
ord-e693c829ed494a03b22abc685af0e9c8
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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