Potassium Carbonate → HCID 69951756, compound

HRID 2300219Notes

Reaction equation

HRID 2300219 reaction equation
[CH2:1]([N:8]([CH:28]1[CH2:31][N:30]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([NH:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH2:29]1)[CH2:9][CH:10]([OH:27])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:47][C:48]([O:50][CH3:51])=[O:49].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)N(C)CCC1.O>[CH3:51][O:50][C:48](=[O:49])[CH2:47][N:41]([C:38]1[CH:37]=[CH:36][C:35]([S:32]([N:30]2[CH2:29][CH:28]([N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH:10]([OH:27])[CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:18]=3)[CH2:31]2)(=[O:34])=[O:33])=[CH:40][CH:39]=1)[CH2:42][CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 18767813HCID 18767813, compound

Product 1

HCID 69951756HCID 69951756, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-{benzyl-[1-(4-butylamino-benzenesulfonyl)-azetidin-3-yl]amino}-3-(4-benzyloxy-phenoxy)-propan-2-ol (0.10 g, 0.15 mmol) in N,N′-dimethylpropyleneurea (1 ml) was added methyl bromoacetate (46 mg, 0.3 mmol) and potassium carbonate (28 mg, 0.2 mmol), and the mixture was stirred at 50° C. for 2 days. It was then cooled to room temperature and diluted with water (20 ml). The aqueous phase was removed, and the residue dissolved in ethyl acetate (20 ml). The organic solution was washed with brine, and dried over anhydrous sodium sulfate. It was then filtered and evaporated, and the residue was chromatographed on silica gel (ethyl acetate-hexanes/1:1) to give 50 mg of a colorless gum; MS (ES) m/z 702.2 (MH+); HRMS (FAB) Calcd. for C39H48N3O7S (MH+): 702.3213, Found: 702.3231.

Workup

  1. temperatureIt was then cooled to room temperature
  2. customThe aqueous phase was removed
  3. dissolutionthe residue dissolved in ethyl acetate (20 ml)
  4. washThe organic solution was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationIt was then filtered
  7. customevaporated
  8. customthe residue was chromatographed on silica gel (ethyl acetate-hexanes/1:1)

Sources & evidence

ORD record
ord-50e1ec97c2f94ab98b4fae8f34824c38
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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