Pyridine → HCID 69451353, compound

HRID 1517164Notes

Reaction equation

HRID 1517164 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.[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCOC(C)=O.CCCCCC>C(#N)C>[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:23]=[CH:24][C:25]([S:28](=[O:29])(=[O:30])[NH:11][CH:7]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:12])[CH:8]([CH3:9])[CH3:10])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 4532027Tert-butyl 2-amino-3-methylbutanoateHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 21226206Ethyl acetate hexane2×

Product 1

HCID 69451353HCID 69451353, compound

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-chlorosulfonyl-benzoic acid methyl ester (670 mg, 2.86 mmol) in acetonitrile (6 ml) was added dropwise and the mixture became slightly yellow coloured and was stirred at ambient temperature for 4 hours. The reaction was monitored by TLC (EtOAc/Hexane, 1:1). The solvents were evaporated and ethyl acetate (50 ml) and saturated sodium bicarbonate solution (10 ml) were added. The mixture was transferred into a separatory funnel and vigorously shaken. Then the phases were separated and the ethyl acetate phase was extracted once with brine (10 ml), dried (MgSO4), 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 880 mg (99.55%).

Workup

  1. customA clear and colourless solution was quickly obtained
  2. customThe solvents were evaporated
  3. additionethyl acetate (50 ml) and saturated sodium bicarbonate solution (10 ml) were added
  4. customThe mixture was transferred into a separatory funnel
  5. stirringvigorously shaken
  6. customThen the phases were separated
  7. extractionthe ethyl acetate phase was extracted once with brine (10 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto afford the crude product

Sources & evidence

ORD record
ord-7cf15fe16e5c4e50b8110f13dfa8bb84
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

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