(R)-4-((1R,4Z,8Z,13R,15R)-15-methoxy-5-methyl-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadeca-4,8-dien-15-yl)-3-(4-methoxybenzyl)thiazolidin-2-one → HCID 24888490, compound

HRID 1664287Notes

Reaction equation

HRID 1664287 reaction equation
COC1C=CC(C[N:8]2[C@H](C34CC(OCC3)CCCC=CCCC(C)=CC(=O)N4)CSC2=O)=CC=1.C[O:36][C@:37]1([C@@H:56]2[CH2:60][S:59][C:58](=[O:61])[N:57]2CC2C=CC(OC)=CC=2)[CH2:52][C@H:51]2[CH2:53][C@@H:39]([CH2:40][CH2:41][CH2:42][CH:43]=[CH:44][CH2:45][CH2:46][C:47]([CH3:55])=[CH:48][C:49](=O)[O:50]2)[O:38]1>>[OH:36][C@:37]1([C@@H:56]2[CH2:60][S:59][C:58](=[O:61])[NH:57]2)[CH2:52][C@H:51]2[CH2:53][C@@H:39]([CH2:40][CH2:41][CH2:42][CH:43]=[CH:44][CH2:45][CH2:46][C:47]([CH3:55])=[CH:48][C:49](=[O:50])[NH:8]2)[O:38]1

Participants

3

Reactant 2

HCID 59644077(R)-4-((1R,4Z,8Z,13R,15R)-15-methoxy-5-methyl-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadeca-4,8-dien-15-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 86641949HCID 86641949, compound

Product 1

HCID 24888490HCID 24888490, compound

Procedure

Application of the method shown in Example 46, with the modification that (1R,4Z,8Z,13R,15R)-15-methoxy-15-(((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-5-methyl-14-oxa-2-aza-bicyclo[11.3.1]heptadeca-4,8-dien-3-one was substituted for (R)-4-((1R,4Z,8Z,13R,15R)-15-methoxy-5-methyl-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadeca-4,8-dien-15-yl)-3-(4-methoxybenzyl)thiazolidin-2-one, afforded the title compound, together with the 8E-isomer.

Sources & evidence

ORD record
ord-3f75da4048074f7fb1e1040c966631d5
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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