Dimethylformamide → HCID 54447215, compound

HRID 2393106Notes

Reaction equation

HRID 2393106 reaction equation
Cl.[NH2:2][CH:3]([C:7]([CH3:11])([CH3:10])[CH2:8][CH3:9])[C:4]([OH:6])=[O:5].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.CN(C=O)C>C1COCC1>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:2][CH:3]([C:7]([CH3:11])([CH3:10])[CH2:8][CH3:9])[C:4]([OH:6])=[O:5])(=[O:31])=[O:30])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 71344521142937-81-3

Product 1

HCID 54447215HCID 54447215, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-amino-3,3-dimethylpentanoic acid hydrochloride (1.63 g), (JCS Chem. Comm. 11, 830-1992) is mixed with diisopropylethylamine (3.6 g, 3.1 equivalent) in dry THF (100 mL). The 4-methoxybenzenesulfonyl chloride (1.86 g, 1 equivalent) is added as a solid. DMF (25 mL) is added to the resulting suspension. After stirring overnight at room temperature the solvents are removed under vacuum. The residue is partitioned between ethyl acetate (200 mL) and 1N HCl (100 mL). The organic phase is separated and the aqueous phase extracted with several more portions of ethyl acetate. The combined organic phases are washed with 1N HCl and then brine. The organic phase are dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting crude product is loaded onto a reverse phase column as a DMSO solution. The column is eluted using a step gradient (10% increments), starting with 30% acetonitrile/water and ending at 90% acetonitrile/water. Combination of the appropriate fractions gave 116 mg of the title compound.

Workup

  1. customare removed under vacuum
  2. customThe residue is partitioned between ethyl acetate (200 mL) and 1N HCl (100 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase extracted with several more portions of ethyl acetate
  5. washThe combined organic phases are washed with 1N HCl
  6. dry with materialThe organic phase are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washThe column is eluted

Sources & evidence

ORD record
ord-d8f0ddf7cbc74d4eb4fc66e62bd1baf9
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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