Nitrogen → HCID 19366833, compound

HRID 849541Notes

Reaction equation

HRID 849541 reaction equation
N#N.[CH3:3][O:4][C:5](=[O:12])[C:6](=[CH2:11])[NH:7][C:8](=[O:10])[CH3:9].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](S)=[CH:17][CH:16]=1.COC(=O)C(CC1C=CC(SOC)=CC=1)NC(=O)C.O[O:42][S:43]([O-:45])=O.[K+]>CO.O.C(N(CC)CC)C>[CH3:3][O:4][C:5](=[O:12])[CH:6]([CH2:11][S:43]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)(=[O:45])=[O:42])[NH:7][C:8](=[O:10])[CH3:9]

Participants

9

Reactant 5

HCID 947NitrogenHCID 127654-MethoxybenzenethiolHCID 98644Methyl 2-acetamidoacrylateHCID 19366820HCID 19366820, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 19366833HCID 19366833, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

Part A: To a stirred degassed (N2) solution of (20 g, 139 mmol) of N-acetyl-dehydroalanine methyl ester in 400 mL of methanol was added (19.5 g, 139 mmol) of 4-methoxythiophenol followed by 14.0 g, 140 mmol) of triethylamine and the resulting solution stirred for 2 hours. The resulting N-acetyl-β-(4-methoxythio-phenyl)-D,L-alanine methyl ester was oxidized in situ by the addition of 800 mL of methanol, 160 mL of water followed by (250 g, 417 mmol) of OXONE®. The suspension was stirred for 3 hours and then filtered through a fritted glass buchner funnel. The filtrate was concentrated by rotary evaporation and the concentrated material was partitioned between ethyl acetate and sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to a white solid which was triturated with cold ethyl acetate and filtered to yield 28.5 g of N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester.

Workup

  1. stirringThe suspension was stirred for 3 hours
  2. filtrationfiltered through a fritted glass buchner funnel
  3. concentrationThe filtrate was concentrated by rotary evaporation
  4. customthe concentrated material was partitioned between ethyl acetate and sodium bicarbonate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid which
  9. customwas triturated with cold ethyl acetate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-2176be4559fe4474adc55862ec27ce56
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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