2,6-Lutidine → HCID 86694358, compound

HRID 538928Notes

Reaction equation

HRID 538928 reaction equation
[OH:1][C@H:2]1[C@H:9]2[C@H:5]([N:6]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[C:7](=[O:10])[O:8]2)[CH2:4][CH2:3]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=O)=O>C(Cl)Cl>[Si:37]([O:1][C@H:2]1[C@H:9]2[C@H:5]([N:6]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[C:7](=[O:10])[O:8]2)[CH2:4][CH2:3]1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86694359HCID 86694359, compound

Product 1

HCID 86694358HCID 86694358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (3aR*,6R*,6aR*)-6-hydroxy-3-((2-nitrophenyl)sulfonyl)hexahydro-2H-cyclo-penta[d]oxazol-2-one (1.2 g, 3.66 mmol) and 2,6-lutidine (0.851 mL, 7.31 mmol) in CH2Cl2 (25 mL) was added dropwise at 0° C. the tert-butyldimethylsilyl trifluoromethanesulfonate (1.091 mL, 4.75 mmol). The reaction mixture was stirred for 1 h at 0° C. followed by 2 h at RT. The reaction mixture was diluted with CH2Cl2 and washed with 20% aqueous NaH2PO4 solution and H2O, dried over MgSO4, filtered and concentrated. The title compound was obtained after crystallization from EtOAc/heptane as white solid (1.5 g, 88%): TLC (heptane/EtOAc 1:1) Rf=0.54; tR=1.58 min (UPLC 1), tR=1.43 min (LC-MS 3); ESI-MS: 460 [M+NH4]+ (LC-MS 3).

Workup

  1. waitfollowed by 2 h at RT
  2. washwashed with 20% aqueous NaH2PO4 solution and H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-90d97ddef7014b20af18a997d4da1bd3
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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