Ethyl Acetate → HCID 86626813, compound

HRID 604057Notes

Reaction equation

HRID 604057 reaction equation
[F:1][C:2]([F:56])([F:55])[C:3]1[CH:4]=[C:5]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[CH2:6][N:7]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=1[N:31]([CH2:46][CH3:47])[C:32](=[O:45])[NH:33][C@@H:34]([CH2:39][O:40]C(C)(C)C)[C:35]([O:37][CH3:38])=[O:36])[C:8]1[N:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][N:9]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>Cl.O1CCOCC1>[F:54][C:51]([F:52])([F:53])[C:49]1[CH:48]=[C:5]([CH:4]=[C:3]([C:2]([F:55])([F:1])[F:56])[CH:50]=1)[CH2:6][N:7]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:22]=1[N:31]([CH2:46][CH3:47])[C:32](=[O:45])[NH:33][C@@H:34]([CH2:39][OH:40])[C:35]([O:37][CH3:38])=[O:36])[C:8]1[N:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86626814HCID 86626814, compound

Product 1

HCID 86626813HCID 86626813, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl (S)-2-[3-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-3-ethyl-ureido]-3-tert-butoxy-propionate (455 mg) is dissolved in a 4N-hydrochloric acid in dioxane (5 ml), and the mixture is stirred at room temperature for 8 hours. To the reaction solution are added a saturated aqueous sodium bicarbonate solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give methyl (S)-2-[3-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-3-ethyl-ureido]-3-hydroxy-propionate (285 mg). MS (m/z): 753 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-1b95ba77245b49928aa50eb37180c175
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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