Water → Latanoprost

HRID 517390Notes

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C@H:9]([OH:28])[CH2:10][CH2:11][C@@H:12]2[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C@@H:15]([OH:26])[CH2:14][C@H:13]2[OH:27])=[CH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].I[CH:36]([CH3:38])[CH3:37].O>CN(C=O)C.C(OCC)(=O)C>[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][CH:36]([CH3:38])[CH3:37])=[O:24])[C@H:12]1[CH2:11][CH2:10][C@@H:9]([OH:28])[CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of crude Latanoprost acid (1.3 g from Example 29) in DMF (13 mL) was treated with K2CO3 (1.38 g, 1.0 mmol) and 2-iodopropane (1.13 g, 6.6 mmol). This mixture was then stirred at 80° C. for 2 hr under an atmosphere of nitrogen (TLC monitoring). Water (40 mL) and ethyl acetate (40 mL) were added and the mixture was stirred for 10 min. The aqueous layer was separated and extracted with ethyl acetate (40 mL), and the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 1.1 g of crude Latanoprost. The crude Latanoprost could be purified by column chromatography and then concentrated under reduced pressure to provide 0.7 g of Latanoprost (60.3% yield, 2 steps; HPLC (Phenomenex Luna 5 μm silica) analysis of the product showed that no isomer was detectable).

Workup

stirringthe mixture was stirred for 10 min
customThe aqueous layer was separated
extractionextracted with ethyl acetate (40 mL)
dry with materialthe combined organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-93481debb9f54214a19c7a3d19d45a07
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115109B2

Reaction notes

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