allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate → HCID 178462305, compound

HRID 1603458Notes

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(OC([N:33]([CH2:38][C:39]1[N:40]2[CH:46]=[N:45][CH:44]=[C:41]2[S:42][CH:43]=1)[S:34]([NH2:37])(=[O:36])=[O:35])=O)C=C>>[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:45]3[CH:44]=[C:41]4[S:42][CH:43]=[C:39]([CH2:38][NH:33][S:34]([NH2:37])(=[O:35])=[O:36])[N+:40]4=[CH:46]3)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9]

Participants

Reactant 2

HCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate

HCID 19605084HCID 19605084, compound

Product 1

HCID 178462305HCID 178462305, compoundYield 2.5%

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 145 mg of 3-[N-allyloxycarbonyl-N-(aminosulfonyl)amino]methyl imidazo[5,1-b]thiazole were used, thereby obtaining 2.8 mg of the title compound.

Sources & evidence

ORD record: ord-0c2c5b886085457c8b0d9ef1865d935a
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990101

Reaction notes

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