Ammonia → HCID 58728741, compound

HRID 1992216Notes

Reaction equation

HRID 1992216 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S(Cl)(=O)=O)C=CC=CC=1.N.C([O:24][C:25](=[O:32])[C:26]([CH3:31])([CH3:30])[C:27](O)=[O:28])C.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1.CN(C)C1C=CN=CC=1.ClCCCl>[CH3:30][C:26]([CH3:31])([C:27](=[O:28])[NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[C:25]([OH:32])=[O:24]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 7369Benzenesulfonyl chlorideHCID 7370Benzenesulfonamide2×HCID 10868DicyclohexylcarbodiimideHCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acid

Product 1

HCID 58728741HCID 58728741, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Benzenesulfonamide was made by adding benzenesulfonyl chloride to a solution of ammonia in tetrahydrofuran and evaporating to a solid. Benzenesulfonamide (87 mg, 0.50 mmole) was added to a shaken suspension of 3-ethoxy-2,2-dimethyl-3-oxopropanoic acid (100 mg, 0.62 mmole) reactivated on PS-DCC resin (1.62 g, 1.25 mmole) and 1.50 mmole of N,N-dimethylpyridin-4-amine in DCE. When reaction is complete the resin is filtered off and the organic layer washed with 1N HCl dried and evaporated. The resulting residue was dissolved in 6 ml of ethanol and 6 ml of 1N LiOH was added and heated to 40° C. The reaction was neutralized with 1N HCl and evaporated to afford 2,2-dimethyl-3-oxo-3-[(phenylsulfonyl)amino]propanoic acid as a crude product which was used with no further purification.

Workup

  1. customevaporating to a solid
  2. customWhen reaction
  3. filtrationis filtered off
  4. washthe organic layer washed with 1N HCl
  5. customdried
  6. customevaporated
  7. dissolutionThe resulting residue was dissolved in 6 ml of ethanol
  8. addition6 ml of 1N LiOH was added
  9. customevaporated

Sources & evidence

ORD record
ord-a4e39f4c82cf4821b6f381cf11f26100
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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