Water → HCID 70006343, compound

HRID 1862638Notes

Reaction equation

HRID 1862638 reaction equation
[NH2:1][C@@H:2]([CH:27]([CH3:29])[CH3:28])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:10]([O:25][CH3:26])[CH:9]=1)=[O:4].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].O>O1CCOCC1>[CH3:37][S:38]([C@@:2]([NH2:1])([CH:27]([CH3:29])[CH3:28])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[C:10]([O:25][CH3:26])[CH:9]=1)=[O:4])(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54099212HCID 54099212, compound

Product 1

HCID 70006343HCID 70006343, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (S)-2-amino-N-(2-{4-[3-(4-chloro-phenyl)-propoxy]-3-methoxy-phenyl}-ethyl)-3-methyl-butyramide (2 g) and triethylamine (0.9 ml) in dioxane (30 ml) is added methanesulfonyl chloride (0.4 ml). The reaction mixture is stirred overnight at room temperature. Water (200 ml) is then added. It is extracted with ethyl acetate (2×200 ml). The organic layers are washed with brine (2×200 ml), dried (MgSO4) and evaporated. (S)-2-Methanesulfonyl-aminoN-(2-{3-methoxy-4-[3-(4-chloro-phenyl)-propoxy]-phenyl}-ethyl)-3-methyl-butyramide is obtained.

Workup

  1. extractionIt is extracted with ethyl acetate (2×200 ml)
  2. washThe organic layers are washed with brine (2×200 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-7d0325cbd7764c979d0eaccf531dd65a
Source dataset
uspto-grants-2003_03
Patent number
US06538159B2

Reaction notes

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