Dimedone → HCID 178462307, compound

HRID 1603462Notes

Reaction equation

HRID 1603462 reaction equation
CC1(C)CC(=O)CC(=O)C1.C(OC([O:17][C@@H:18]([C@H:20]1[C:35](=[O:36])[N:22]2[C:23]([C:29]([O:31]CC=C)=[O:30])=[C:24]([CH2:27]O)[C@H:25]([CH3:26])[C@H:21]12)[CH3:19])=O)C=C.C(OC([NH:43][CH2:44][CH2:45][NH:46][C:47]([C:49]1[N:50]2[CH:56]=[N:55][CH:54]=[C:51]2[S:52][CH:53]=1)=[O:48])=O)C=C>>[OH:17][C@@H:18]([C@H:20]1[C:35](=[O:36])[N:22]2[C:23]([C:29]([O-:31])=[O:30])=[C:24]([CH2:27][N:55]3[CH:54]=[C:51]4[S:52][CH:53]=[C:49]([C:47](=[O:48])[NH:46][CH2:45][CH2:44][NH2:43])[N+:50]4=[CH:56]3)[C@H:25]([CH3:26])[C@H:21]12)[CH3:19]

Participants

4

Reactant 3

HCID 31358DimedoneHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 19605200HCID 19605200, compound

Product 1

HCID 178462307HCID 178462307, compoundYield 5.4%

Procedure

The same procedure as in Example 1 was repeated except that dimedone was used as a trapping agent in a deprotective reaction, and 145 mg of allyl (1S,5R,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate and 340 mg of 3-[N-(2-allyloxycarbonylaminoethyl)carbamoyl]imidazo[5,1-b]thiazole were used, thereby obtaining 9.3 mg of the title compound.

Sources & evidence

ORD record
ord-bf9d9c781db44d579675a2fa6b774918
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…