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

HRID 1603459Notes

Reaction equation

HRID 1603459 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.[NH:27]([CH2:31][C:32]1[N:33]2[CH:39]=[N:38][CH:37]=[C:34]2[S:35][CH:36]=1)[C:28]([NH2:30])=[O:29]>>[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:38]3[CH:37]=[C:34]4[S:35][CH:36]=[C:32]([CH2:31][NH:27][C:28]([NH2:30])=[O:29])[N+:33]4=[CH:39]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 196051393-Ureidomethylimidazo[5,1-b]thiazole

Product 1

HCID 178462301(1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(3-ureidomethylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylateYield 3.9%

Procedure

The same procedure as in Example 1 was repeated except that 135 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 87 mg of 3-ureidomethylimidazo[5,1-b]thiazole were used, thereby obtaining 6 mg of the title compound.

Sources & evidence

ORD record
ord-1a8ebd65ceaa4c4bbb32ecc13fa213cf
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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