Sodium Bicarbonate → HCID 67315296, compound

HRID 2059898Notes

Reaction equation

HRID 2059898 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C@@H:7]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]([OH:10])=[O:9].[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28](Cl)(=[O:30])=[O:29])=[C:23]([CH3:32])[CH:22]=1>O1CCOCC1.O.O1CCOCC1>[C:15]([O:14][C:12](=[O:13])[CH2:11][C@H:7]([NH:6][S:28]([C:24]1[C:25]([CH3:27])=[CH:26][C:21]([O:20][CH3:19])=[CH:22][C:23]=1[CH3:32])(=[O:30])=[O:29])[C:8]([OH:10])=[O:9])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 70105704-tert-Butyl hydrogen L-aspartateHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 67315296HCID 67315296, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Sodium bicarbonate (1.5 eq) was added to a suspension of (S)-2-amino-4-tert-butoxy-4-oxobutanoic acid (5.1 mmol, 1.2 eq) in dioxane/water (1:1, 20 ml) and the mixture was stirred for 30 min at room temperature. A solution of 4-methoxy-2,6-dimethylbenzenesulfonic acid chloride (4.3 mmol, 1.0 eq) in dioxane (10 ml) was added and the reaction mixture stirred for 16 h at room temperature. On completion of the reaction the organic solvent was removed under vacuum and the aqueous phase acidified with 10% HCl (eq). Extraction was then performed with DCM and the organic phase was washed with saturated sodium chloride solution, dried (Na2SO4) and concentrated to small volume under vacuum. Yield: 45%.

Workup

  1. stirringthe reaction mixture stirred for 16 h at room temperature
  2. customOn completion of the reaction the organic solvent
  3. customwas removed under vacuum
  4. extractionExtraction
  5. washthe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-975c9a98af4e43d4a31fa763b887bb14
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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