Water → (2S,3S)-2-(butylsulfonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]ethyl}-amide

HRID 650973Notes

Reaction equation

HRID 650973 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][CH2:22][NH:23][C:24](=[O:31])[C@@H:25]([NH2:30])[C@@H:26]([CH3:29])[CH2:27][CH3:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[CH2:39]([S:43](Cl)(=[O:45])=[O:44])[CH2:40][CH2:41][CH3:42].O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][CH2:22][NH:23][C:24](=[O:31])[C@@H:25]([NH:30][S:43]([CH2:39][CH2:40][CH2:41][CH3:42])(=[O:45])=[O:44])[C@@H:26]([CH3:29])[CH2:27][CH3:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 57011389(2S,3S)-2-amino-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

Product 1

HCID 57032289(2S,3S)-2-(butylsulfonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]ethyl}-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.4 g of (2S,3S)-2-amino-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide and 1.2 ml of triethylamine are placed in 50 ml of dioxane at room temperature. 1.0 ml of n-butylsulfonyl chloride is added thereto. Stirring is carried out for 16 hours. The reaction mixture is introduced into 200 ml of water. Extraction is carried out twice using 200 ml of ethyl acetate each time. The organic phases are washed once with 200 ml of saturated sodium chloride solution, combined, dried over magnesium sulfate and concentrated, yielding (2S,3S)-2-(butylsulfonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]ethyl}-amide, which can be purified by chromatography on silica gel with ethyl acetatein-hexane =1:1, in the form of an oil.

Workup

  1. extractionExtraction
  2. washThe organic phases are washed once with 200 ml of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-30533c58bd224a4ebb8e102f769d1e72
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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