Pyridine → Tert-butyl 2-{[(4-methoxyphenyl)sulfonyl]amino}-3-methylbutanoate

HRID 1517166Notes

Reaction equation

HRID 1517166 reaction equation
[C:1]([O:5][C:6](=[O:12])[CH:7]([NH2:11])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[O:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH3:20].CCOC(C)=O.CCCCCC>C(#N)C>[C:1]([O:5][C:6](=[O:12])[CH:7]([NH:11][S:27]([C:24]1[CH:23]=[CH:22][C:21]([O:19][CH3:20])=[CH:26][CH:25]=1)(=[O:29])=[O:28])[CH:8]([CH3:9])[CH3:10])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 4532027Tert-butyl 2-amino-3-methylbutanoateHCID 21226206Ethyl acetate hexane2×

Product 1

HCID 10783604Tert-butyl 2-{[(4-methoxyphenyl)sulfonyl]amino}-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of 2-Amino-3-methyl-butyric acid tert-butyl ester (H-D-Val-OtBu.HCl) (500 mg, 2.38 mmol) in acetonitrile (20 ml) was added pyridine (767 μl, 9.52 mmol) at ambient temperature. A clear and colourless solution was quickly obtained. Then a solution of 4-methoxyl-benzenesulfonyl chloride (541 mg, 2.62 mmol) in acetonitrile (10 ml) was added dropwise and the mixture became slightly yellow coloured and was stirred at ambient temperature. TLC (EtOAc/Hexane, 1:1) monitoring showed the reaction was completed after 3 hours. After evaporation of acetonitrile, the residue was taken up in dichloromethane (30 ml) and extracted once each with 10% sodium bicarbonate solution (30 ml) and water (30 ml). Then the phases were separated and the dichloromethane phase was dried (Na2SO4), filtered and evaporated to afford the crude product. Flash chromatography using (Ethyl acetate/Hexane, 1:1) gave the pure product as a white solid. Yield 801 mg (93.90%).

Workup

  1. customA clear and colourless solution was quickly obtained
  2. customAfter evaporation of acetonitrile
  3. extractionextracted once each with 10% sodium bicarbonate solution (30 ml) and water (30 ml)
  4. customThen the phases were separated
  5. dry with materialthe dichloromethane phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product

Sources & evidence

ORD record
ord-72713618cb984aecb7fb08f4cda37ee3
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

Loading…