Methanol → HCID 42643386, compound

HRID 1162630Notes

Reaction equation

HRID 1162630 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH2:22][O:23]S(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][O-].[Na+].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH2:22][O:23][CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium Methoxide2×HCID 42643385HCID 42643385, compound

Product 1

HCID 42643386HCID 42643386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18.1 To a stirred solution of 200 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (example 17.2) at r.t. in 5 ml THF under an argon atmosphere were added 78 mg sodium methylate. The resulting suspension was heated to reflux for 4 hrs, then treated again with 78 mg sodium methylate and 1.5 ml MeOH and refluxed overnight. The reaction mixture was cooled to r.t. and concentrated. The crude product was purified by column chromatography (silica gel, gradient: cyclohexane->cyclohexane/EtOAc 35:65) to give (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless gum. MS 375.0 ([M+H]+)

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 4 hrs
  3. temperaturerefluxed overnight
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel, gradient: cyclohexane->cyclohexane/EtOAc 35:65)

Sources & evidence

ORD record
ord-b06125466da740d1ba7d631b88babcae
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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