Methanol → 73275-76-0

HRID 1482736Notes

Reaction equation

HRID 1482736 reaction equation
[CH:1]1[CH:2]=[C:3]([C:29]([F:32])([F:31])[F:30])[CH:4]=[C:5]([O:7][CH2:8][CH:9]([OH:28])/[CH:10]=[CH:11]/[CH:12]2[CH:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:15]([OH:26])[CH2:14][CH:13]2[OH:27])[CH:6]=1.[CH3:33]O>CC(O)=O>[OH:27][C@@H:13]1[CH2:14][C@H:15]([OH:26])[C@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:33])=[O:24])[C@H:12]1/[CH:11]=[CH:10]/[C@@H:9]([OH:28])[CH2:8][O:7][C:5]1[CH:6]=[CH:1][CH:2]=[C:3]([C:29]([F:31])([F:30])[F:32])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 20838310HCID 20838310, compound

Product 1

HCID 4436644273275-76-0

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To fluprostenol in MeOH at 0° C. was added TMS-CH2N2 until the solution persisted a yellow color. AcOH (2 drops) were added to quench excess TMS-CH2N2 and the solvents were evaporated. Column chromatography 90%-100% EtOAc/Hexanes gave pure (Z)-methyl 7-((1R,2R,3R,5 S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate (9).

Workup

  1. customto quench excess TMS-CH2N2
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-20b32909deed45838651b5b7c335ec4a
Source dataset
uspto-grants-2016_08
Patent number
US09415043B2

Reaction notes

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