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Perchloric Acid → 3-{2-[(2R,3R,4S,5R)-4,5-dihydroxy-2-{2-[4-(6-methoxypyridin-3-yl)phenyl]ethyl}tetrahydrofuran-3-yl]ethyl}-1,2,3-benzotriazin-4(3H)-one

HRID 84002
Notes
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Reaction equation

HRID 84002 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C@H:22]3[O:31][C@H:25]4[O:26]C(C)(C)[O:28][C@H:24]4[C@H:23]3[CH2:32][CH2:33][N:34]3[C:39](=[O:40])[C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[N:36]=[N:35]3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>C(#N)C.C(OCC)(=O)C.O>[OH:28][C@@H:24]1[C@H:25]([OH:26])[O:31][C@H:22]([CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([C:11]3[CH:12]=[N:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)[C@@H:23]1[CH2:32][CH2:33][N:34]1[C:39](=[O:40])[C:38]2[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=2[N:36]=[N:35]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24247Perchloric AcidHCID 671822143-{2-[(3aS,5R,6S,6aS)-5-{2-[4-(6-methoxypyridin-3-yl)phenyl]ethyl}-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]ethyl}-1,2,3-benzotriazin-4(3H)-one

Product 1

HCID 671825273-{2-[(2R,3R,4S,5R)-4,5-dihydroxy-2-{2-[4-(6-methoxypyridin-3-yl)phenyl]ethyl}tetrahydrofuran-3-yl]ethyl}-1,2,3-benzotriazin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
2×
HCID 6342AcetonitrileSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Perchloric acid (4.8 mL) was added to a solution of the compound obtained from step c above (8.1 g) in acetonitrile (50 mL) and water (8 mL) at room temperature. The reaction mixture was heated to 55° C. for 30 minutes. The reaction mixture was then quenched using sodium bicarbonate solution. The solvents were evaporated under reduced pressure. The residue thus obtained was taken up in ethyl acetate and water. The organic layer was separated, washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was concentrated under reduced pressure to yield the title compound (8 g).

Workup

  1. customat room temperature
  2. customThe reaction mixture was then quenched
  3. customThe solvents were evaporated under reduced pressure
  4. customThe residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with water and brine solution
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1836a01bcacd47f8b9f1257fb990bd0b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846910B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes