Isopropyl iodide → Latanoprost

HRID 468037Notes

Reaction equation

HRID 468037 reaction equation
[CH3:1][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:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:16]([OH:30])[CH2:15][C@@H:14]1[OH:31])=[O:6])[CH3:3].N[C@H](C(O)=O)CCCNC(=N)N.C(I)(C)C.C([O-])(=O)C.[NH4+].C(OCC)(=O)C>CO.O>[CH3:3][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:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:16]([OH:30])[CH2:15][C@@H:14]1[OH:31])=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 178459547HCID 178459547, compound

Product 1

HCID 5311221Latanoprost

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To 1.0 gram of Latanoprost L-arginine salt (2) in MeOH/H2O (4:1, 20 mL) is added 2.01 equivalents of isopropyl iodide (99%, Cat #148938, Sigma-Aldrich, St. Louis, Mo.). and the solution is stirred overnight. Saturated aqueous ammonium acetate is added along with ethyl acetate and the layers are separated. The organic layer is separated, and the solvents removed in vaccuo, and the material is chromatographed to give latanoprost as the isopropyl ester (6).

Workup

  1. customthe layers are separated
  2. customThe organic layer is separated
  3. customthe solvents removed in vaccuo
  4. customthe material is chromatographed

Sources & evidence

ORD record
ord-9dac1f0b06f54da286837923ab096894
Source dataset
uspto-grants-2014_01
Patent number
US08623918B2

Reaction notes

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