tert-Butanol → HCID 86670146, compound

HRID 2169603Notes

Reaction equation

HRID 2169603 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, 9 H), 3.00-3.10 (m, 1 H), 3.15-3.28 (m, 2 H), 3.37 (dd, J=11.37, 8.84 Hz, 1 H), 3.52-3.62 (m, 1 H), 3.64-3.75 (m, 2 H), 3.86-4.06 (m, 3 H), 4.52 (dd, J=13.77, 1.89 Hz, 1 H), 7.22 (s, 1 H); 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-06f1f0802c0a418a9dfd0c79742101a9
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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