Triethylamine → HCID 59045569, compound

HRID 1862496Notes

Reaction equation

HRID 1862496 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]/[CH:16]=[CH: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([CH2:35][CH3:36])CC)C.[S:37](Cl)(O)(=[O:39])=[O:38].CC>O1CCOCC1.[Cl-].[Na+].O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18](/[CH:17]=[CH:16]\[CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][NH:5][C:3](=[O:4])[C@@H:2]([NH:1][S:37]([CH2:35][CH3:36])(=[O:39])=[O:38])[CH:27]([CH3:29])[CH3:28])=[CH:9][C:10]=2[O:25][CH3:26])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18619828HCID 18619828, compoundHCID 69822851HCID 69822851, compound

Product 1

HCID 59045569HCID 59045569, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To Z-(S)-2-amino-N-(2-{4-[3-(4-chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethyl)-3-methyl-butyramide (1.7 g), and triethylamine (1 g) in dioxane (30 ml) is added ethane sulfochloride (0.52 g). The mixture is stirred at room temperature for 16 hours. Brine (200 ml) is added. It is extracted with ethyl acetate (2×200 ml). The organic layers are washed with brine (100 ml) dried and evaporated. The residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:1) and recrystallised. Z-(S)-N-(2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethyl)-2-ethanesulfonylamino-3-methyl-butyramide is obtained, m.p. 141-143° C.

Workup

  1. extractionIt is extracted with ethyl acetate (2×200 ml)
  2. washThe organic layers are washed with brine (100 ml)
  3. customdried
  4. customevaporated
  5. customThe residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:1)
  6. customrecrystallised

Sources & evidence

ORD record
ord-9b1a20b7f3564fcfbc909852a62b7931
Source dataset
uspto-grants-2003_03
Patent number
US06538016B2

Reaction notes

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