Latanoprost → 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, methyl ester, (5Z)-

HRID 1482735Notes

Reaction equation

HRID 1482735 reaction equation
C[CH:2]([O:4][C:5]([CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]1[C@@H:17]([CH2:18][CH2:19][C@@H:20]([OH:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:16]([OH:30])[CH2:15][C@@H:14]1[OH:31])=[O:6])C>CO.CC(O)=O>[OH:30][C@@H:16]1[CH2:15][C@H:14]([OH:31])[C@H:13]([CH2:12]/[CH:11]=[CH:10]\[CH2:9][CH2:8][CH2:7][C:5]([O:4][CH3:2])=[O:6])[C@H:17]1[CH2:18][CH2:19][C@@H:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 5311221Latanoprost

Product 1

HCID 597875295-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, methyl ester, (5Z)-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To Latanoprost free acid 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 70%-100% EtOAc/Hexanes gave pure (Z) -methyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy -5-phenylpentyl)cyclopentyl)hept-5-enoate (2).

Workup

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

Sources & evidence

ORD record
ord-35f8fbb42bff475bad7aa67839bd65ba
Source dataset
uspto-grants-2016_08
Patent number
US09415043B2

Reaction notes

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