Latanoprost → HCID 178459547, compound

HRID 468034Notes

Reaction equation

HRID 468034 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: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])[CH3:3].[NH2:32][C@H:33]([C:41]([OH:43])=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39]>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: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])[CH3:1].[NH2:32][C@H:33]([C:41]([OH:43])=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40]

Participants

4

Reactant 2

HCID 5311221LatanoprostHCID 178418600HCID 178418600, compound

Product 1

HCID 178459547HCID 178459547, compound

Reagents, catalysts & solvents 1

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

Procedure

To Latanoprost (free acid) (1, 21.2 mg, 0.054 mmol) in MeOH/H2O (4:1, 0.65 mL) was added L-Arginine (72 mM solution in MeOH/H2O [4:1]) (754 μL, 0.054 mmol) ((>98%) from Sigma-Aldrich Cat. A5006) and the solution was stirred for 30 minutes. The solvents were evaporated then azeotroped with Et2O and hexanes to give white crystalline Latanoprost-L-Arginine salt 2 (quantitative).

Workup

  1. customThe solvents were evaporated
  2. customthen azeotroped with Et2O and hexanes

Sources & evidence

ORD record
ord-f9db36b4bb72452ba9bc607472ecf2c6
Source dataset
uspto-grants-2014_01
Patent number
US08623918B2

Reaction notes

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