(R)-4-((1R,13R,15R)-15-Methoxy-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadecan-15-yl)-3-(4-methoxybenzyl)thiazolidin-2-one → (R)-4-((1R,13R,15R)-15-Hydroxy-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadecan-15-yl)thiazolidin-2-one

HRID 1664271Notes

Reaction equation

HRID 1664271 reaction equation
C[O:2][C@:3]1([C@@H:21]2[CH2:25][S:24][C:23](=[O:26])[N:22]2CC2C=CC(OC)=CC=2)[CH2:18][C@H:17]2[CH2:19][C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:20])[O:16]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:21]2[CH2:25][S:24][C:23](=[O:26])[NH:22]2)[CH2:18][C@H:17]2[CH2:19][C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:20])[O:16]2)[O:4]1

Participants

3

Reactant 2

HCID 59644041(R)-4-((1R,13R,15R)-15-Methoxy-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadecan-15-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 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 24888494(R)-4-((1R,13R,15R)-15-Hydroxy-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadecan-15-yl)thiazolidin-2-one

Procedure

Application of the method shown in Example 46, with the modification that (R)-4-((1R,13R,15R)-15-methoxy-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadecan-15-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-24e73114dbf944d9b2ebbb91fdf13eb7
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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