HCID 131733342, compound → HCID 131733341, compound

HRID 517377Notes

Reaction equation

HRID 517377 reaction equation
[CH2:1]([Si:3]([CH2:48][CH3:49])([CH2:46][CH3:47])[O:4][C@@H:5]1[CH2:9][C@H:8]([OH:10])[C@H:7]([CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([O:19]C(C)C)=[O:18])[C@H:6]1/[CH:23]=[CH:24]/[C@@H:25]([O:38][Si:39]([CH2:44][CH3:45])([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)[CH3:2]>C(C(C)=O)C(C)C>[F:37][C:34]([F:35])([F:36])[C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[O:27][CH2:26][C@H:25]([O:38][Si:39]([CH2:40][CH3:41])([CH2:42][CH3:43])[CH2:44][CH3:45])/[CH:24]=[CH:23]/[C@H:6]1[C@H:5]([O:4][Si:3]([CH2:1][CH3:2])([CH2:48][CH3:49])[CH2:46][CH3:47])[CH2:9][C@H:8]([OH:10])[C@@H:7]1[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

3

Reactant 1

HCID 131733342HCID 131733342, compound

Product 1

HCID 131733341HCID 131733341, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

(Z)-isopropyl 7-((1R,2R,3R,5S)-3-((triethylsilyl)oxy)-2-((R,E)-3-((triethylsilyl)oxy)-4-(3-(trifluoro methyl)phenoxy)but-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoate (1.5 g from Example 14) in 10 mL methyl isobutyl ketone and 0.2 g Candida antarcitica lipase was added into 25 mL round-bottom flask. The reaction mixture was stirred at room temperature for 3 days. Then, the Lipase was filtered off and solvent was evaporated off under vacuum to obtain 1.5 g crude product.

Workup

  1. filtrationThen, the Lipase was filtered off
  2. customsolvent was evaporated off under vacuum

Sources & evidence

ORD record
ord-5160b40f52414ca3add9b60561757ae8
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

Loading…