Hydrochloric Acid → HCID 69137967, compound

HRID 842991Notes

Reaction equation

HRID 842991 reaction equation
[CH2:1](I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=O)([O-])[O-].[K+].[K+].[CH2:15]([N:22]([CH:28]([CH:32]([CH3:34])[CH3:33])[C:29]([O-:31])=[O:30])[S:23]([NH:26][CH3:27])(=[O:25])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CN(C=O)C>[CH2:15]([N:22]([S:23]([NH:26][CH2:27][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:25])=[O:24])[C@H:28]([CH:32]([CH3:34])[CH3:33])[C:29]([O:31][CH3:9])=[O:30])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12098Benzyl iodideHCID 131721477HCID 131721477, compound

Product 1

HCID 69137967HCID 69137967, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl iodide (280 mg, 1.28 mmol) and anhydrous potassium carbonate (440 mg, 3.2 mmol) were added to a solution of methyl 2-(R)-([benzyl-(methylaminosulfonyl)amino]-3-methylbutyrate (200 mg, 0.64 mmol), [prepared as described in Step 1 above] in DMF (3 ml) at RT. After 96 h, 1 M HCl was added and the product was extracted into ethyl acetate. The organic layer was washed with dilute sodium thiosulfate and brine and dried over MgSO4. The organics were removed in vacuo and the residue was chromatographed (PTLC, SiO2, 20% ethyl acetate/hexane) to give methyl 2-(R)-[benzyl-(benzylmethylaminosulfonyl)amino]-3-methylbutyrate as a colorless oil (60%).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe organic layer was washed with dilute sodium thiosulfate and brine
  3. dry with materialdried over MgSO4
  4. customThe organics were removed in vacuo
  5. customthe residue was chromatographed (PTLC, SiO2, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e8925b6e561749f3995960fe66acb6a1
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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