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Methanol → Esomeprazolemagnesiumtrihydrate

HRID 1375523
Notes
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Reaction equation

HRID 1375523 reaction equation
[Mg:1].ClCCl.C[OH:6].[CH3:7][C:8]1[CH:9]=[N:10][C:11]([CH2:17][S+:18]([O-:30])[C:19]2[NH:20][C:21]3[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[N:27]=2)=[C:12]([CH3:16])[C:13]=1[O:14][CH3:15]>O>[CH3:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([CH3:16])[C:11]([CH2:17][S:18]([C:19]2[N-:20][C:21]3[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[N:27]=2)=[O:30])=[N:10][CH:9]=1.[CH3:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([CH3:16])[C:11]([CH2:17][S:18]([C:19]2[N-:20][C:21]3[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[N:27]=2)=[O:30])=[N:10][CH:9]=1.[OH2:6].[OH2:14].[OH2:14].[Mg+2:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 5462224MagnesiumHCID 178488147HCID 178488147, compound

Product 1

HCID 130565Esomeprazolemagnesiumtrihydrate

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

Magnesium metal (1.33 grams) and Dichloromethane (3.7 ml) were added to methanol (111 ml) and stirred for 1–2 hours. The mass was cooled to a temperature of 5–10° C., esomeprazole obtained in Example 2 (37.0 grams) and methanol (111.0 ml) were added accompanied by stirring for 15–30 minutes. The reaction mass was decomposed into water (666 ml) at a temperature of 5–10° C. over a period of 45–60 minutes, and then further stirred for 30–45 minutes to separate the solid mass. The solid mass was filtered, and washed with water (222 ml). The thus obtained compound was dissolved in methanol (222 ml), and filtered off the solution to separate any excess magnesium. The solvent was removed from the filtrate to get the residual mass. The residual mass was crystallized in Acetone (278 ml) at a temperature of 0–5° C. to afford optically pure Esomeprazole magnesium trihydrate salt. The resulting product had the following characteristics. Weight: 11.5 g. Chiral Purity: ˜100%. Optical rotation: −125° (c=0.5% methanol)

Workup

  1. additionwere added
  2. stirringby stirring for 15–30 minutes
  3. stirringfurther stirred for 30–45 minutes
  4. customto separate the solid mass
  5. filtrationThe solid mass was filtered
  6. washwashed with water (222 ml)
  7. dissolutionThe thus obtained compound was dissolved in methanol (222 ml)
  8. filtrationfiltered off the solution
  9. customto separate any excess magnesium
  10. customThe solvent was removed from the filtrate
  11. customto get the residual mass
  12. customThe residual mass was crystallized in Acetone (278 ml) at a temperature of 0–5° C.

Sources & evidence

ORD record
ord-32a568bef4a64a6fa39c472f7941fa66
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169793B2

Reaction notes

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