Triethylamine → HCID 178488147, compound

HRID 1817286Notes

Reaction equation

HRID 1817286 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9]([S:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:12])=[N:10][C:6]=2[CH:5]=1.C([C@](C([O-])=O)(O)[C@](CC)(O)C([O-])=O)C.C(N(CC)CC)C.C(O)(=O)[C@H](C1C=CC=CC=1)O>CC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:23][C:17]1[CH:16]=[N:15][C:14]([CH2:13][S+:11]([O-:12])[C:9]2[NH:8][C:7]3[CH:24]=[CH:25][C:4]([O:3][CH3:2])=[CH:5][C:6]=3[N:10]=2)=[C:19]([CH3:20])[C:18]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 439616(S)-mandelic acidHCID 29414049diethyl-D-tartarateHCID 178488156HCID 178488156, compound

Product 1

HCID 178488147HCID 178488147, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 180AcetoneSolvent2×

Procedure

The procedure was carried out as described in Raju et al, Organic Process Research & Development 2006, 10, 33-35, which is hereby incorporated by reference in its entirety. To a suspension of omeprazole sodium salt (5.53 g, 15.1 mmol, 1 equiv) in acetone (60 mL), were added a solution of diethyl-D-tartrate (3.1 g, 15.1 mol, 1 equiv) in acetone (3 mL), titanium (IV) isopropoxide (2.14 g, 7.55 mmol, 0.5 equiv) and triethylamine (4.75 g, 45.3 mmol, 3 equiv) at 35-40° C. To the resulting homogeneous solution was added L-(+)-mandelic acid (2.64 g, 17.4 mmol, 1.15 equiv). The mixture was cooled to ambient temperature and stirred for about 1-2 hours. The precipitate was filtered, washed with acetone (30 mL), and dried under reduced pressure to afford esomeprazole mandalate salt.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with acetone (30 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a331987f5f5c4b39ac0b2dead2adf1b7
Source dataset
uspto-grants-2009_10
Patent number
US07598273B2

Reaction notes

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