(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 → (Z)-((2R,4R,6R)-2-Hydroxy-2-((R)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

HRID 1445395Notes

Reaction equation

[CH3:1]/[C:2](/[CH2:38][CH2:39][CH:40]=[CH2:41])=[CH:3]/[C:4]([O:6][C@@H:7]1[CH2:12][C@@H:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:10][C@@:9]([O:36]C)([C@@H:21]2[CH2:25][S:24][C:23](=[O:26])[N:22]2CC2C=CC(OC)=CC=2)[CH2:8]1)=[O:5].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>>[CH3:1]/[C:2](/[CH2:38][CH2:39][CH:40]=[CH2:41])=[CH:3]/[C:4]([O:6][C@@H:7]1[CH2:12][C@@H:11]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:10][C@@:9]([OH:36])([C@@H:21]2[CH2:25][S:24][C:23](=[O:26])[NH:22]2)[CH2:8]1)=[O:5]

Participants

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-one

HCID 59644081(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

Product 1

HCID 24888315(Z)-((2R,4R,6R)-2-Hydroxy-2-((R)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

Procedure

Application of the method shown in Example 46, with the modification that (Z)-((2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl) 3-methylhepta-2,6-dienoate is 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, affords the title compound.

Sources & evidence

ORD record: ord-3b3ac16f3033493cad0373289383f19f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666861B2

Reaction notes

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