allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate → HCID 178462298, compound

HRID 1603457Notes

Reaction equation

HRID 1603457 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]([O:30][CH2:31][CH2:32][C:33]1[N:34]2[CH:40]=[N:39][CH:38]=[C:35]2[S:36][CH:37]=1)(=[O:29])[NH2:28]>>[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:39]3[CH:38]=[C:35]4[S:36][CH:37]=[C:33]([CH2:32][CH2:31][O:30][C:27](=[O:29])[NH2:28])[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 19605108HCID 19605108, compound

Product 1

HCID 178462298HCID 178462298, compoundYield 23.8%

Procedure

The same procedure as in Example 1 was repeated except that 95 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 110 mg of 3-(2-carbamoyloxyethyl)imidazo[5,1-b]thiazole were used, thereby obtaining 26.9 mg of the title compound.

Sources & evidence

ORD record
ord-e06ba35823fa46d69675c03abee1f078
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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