(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-pentyl-tetrahydro-2H-pyran-4-yl) 3-Methylhept-2-enoate → (Z)-((2R,4R,6R)-2-Hydroxy-2-((R)-2-oxothiazolidin-4-yl)-6-pentyl-tetrahydro-2H-pyran-4-yl) 3-Methylhept-2-enoate

HRID 2251791Notes

Reaction equation

HRID 2251791 reaction equation
C[O:2][C@:3]1([C@@H:24]2[CH2:28][S:27][C:26](=[O:29])[N:25]2CC2C=CC(OC)=CC=2)[CH2:8][C@H:7]([O:9][C:10](=[O:18])/[CH:11]=[C:12](/[CH3:17])\[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6][C@@H:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[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:24]2[CH2:28][S:27][C:26](=[O:29])[NH:25]2)[CH2:8][C@H:7]([O:9][C:10](=[O:18])/[CH:11]=[C:12](/[CH3:17])\[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6][C@@H:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:4]1

Participants

3

Reactant 2

HCID 59644073(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-pentyl-tetrahydro-2H-pyran-4-yl) 3-Methylhept-2-enoateHCID 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 46213890(Z)-((2R,4R,6R)-2-Hydroxy-2-((R)-2-oxothiazolidin-4-yl)-6-pentyl-tetrahydro-2H-pyran-4-yl) 3-Methylhept-2-enoate

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-pentyl-tetrahydro-2H-pyran-4-yl)-3-methylhept-2-enoate 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-1de7014e070d4d4d98b69669d18a2315
Source dataset
uspto-grants-2008_01
Patent number
US07320974B2

Reaction notes

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