(R)-4-((1R,14R,16R)-16-Methoxy-3-oxo-2,15-dioxa-bicyclo[12.3.1]octadecan-16-yl)-3-(4-methoxybenzyl)thiazolidin-2-one → (R)-4-((1R,14R,16R)-16-Hydroxy-3-oxo-2,15-dioxa-bicyclo[12.3.1]octadecan-16-yl)thiazolidin-2-one

HRID 1664272Notes

Reaction equation

C[O:2][C@:3]1([C@@H:22]2[CH2:26][S:25][C:24](=[O:27])[N:23]2CC2C=CC(OC)=CC=2)[CH2:19][C@H:18]2[CH2:20][C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:21])[O:17]2)[O:4]1.CO[C@]1([C@@H]2CSC(=O)N2CC2C=CC(OC)=CC=2)C[C@H]2C[C@@H](CCCC=CCCC(C)=CC(=O)O2)O1>>[OH:2][C@:3]1([C@@H:22]2[CH2:26][S:25][C:24](=[O:27])[NH:23]2)[CH2:19][C@H:18]2[CH2:20][C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:21])[O:17]2)[O:4]1

Participants

Reactant 2

HCID 58712855(R)-4-((1R,14R,16R)-16-Methoxy-3-oxo-2,15-dioxa-bicyclo[12.3.1]octadecan-16-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

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-one

Product 1

HCID 59644065(R)-4-((1R,14R,16R)-16-Hydroxy-3-oxo-2,15-dioxa-bicyclo[12.3.1]octadecan-16-yl)thiazolidin-2-one

Procedure

Application of the method shown in Example 46, with the modification that (R)-4-((1R,14R,16R)-16-methoxy-3-oxo-2,15-dioxa-bicyclo[12.3.1]octadecan-16-yl)-3-(4-methoxybenzyl)thiazolidin-2-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.

Sources & evidence

ORD record: ord-744ce330c4ca4cff83c11b1776b9aa76
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039465B2

Reaction notes

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