tert-Butanol → HCID 86670146, compound

HRID 1631762Notes

Reaction equation

HRID 1631762 reaction equation
CC(C)([O-])C.[K+].C(O)(C)(C)C.[Cl:12][C:13]1[N:22]=[CH:21][C:20]2[NH:19][CH2:18][C@H:17]3[CH2:23][O:24][CH2:25][CH2:26][N:16]3[C:15]=2[N:14]=1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C.O>[Cl:12][C:13]1[N:22]=[CH:21][C:20]2[N:19]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:18][C@H:17]3[CH2:23][O:24][CH2:25][CH2:26][N:16]3[C:15]=2[N:14]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 86670147HCID 86670147, compound

Product 1

HCID 86670146HCID 86670146, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide in tert-BuOH (1M, 2.65 mL, 2.65 mmol) was added to a solution of (S)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x4, 500 mg, 2.206 mmol) in DMF (5 mL) at 0° C. The resultant mixture was stirred at room temperature for 30 minutes. tert-Butyl 2-bromoacetate (0.421 mL, 2.87 mmol) was added to the reaction mixture at 0° C. The resultant mixture was stirred at room temperature for 1 hour. After addition of water, the resultant mixture was extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash column chromatography (gradient 20-80% EtOAc/hexane) to afford the title compound as an off-white solid (415 mg, 55.2%). 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (s, 9H), 3.00-3.10 (m, 1H), 3.15-3.28 (m, 2H), 3.37 (dd, J=11.37, 8.84 Hz, 1H), 3.52-3.62 (m, 1H), 3.64-3.75 (m, 2H), 3.86-4.06 (m, 3H), 4.52 (dd, J=13.77, 1.89 Hz, 1H), 7.22 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H21ClN4O3, 341.14. found 341.2.

Workup

  1. extractionthe resultant mixture was extracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash column chromatography (gradient 20-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-f429e50ac8a74befa5a1724563dc8653
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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