HCID 86694360, compound → HCID 86694359, compound

HRID 538929Notes

Reaction equation

HRID 538929 reaction equation
[C@H:1]12[O:6][C@H:5]1[CH2:4][CH2:3][C@@H:2]2[N:7]([S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:8](=[O:14])[O:9]C(C)(C)C>CO>[OH:6][C@H:5]1[C@H:1]2[C@H:2]([N:7]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-:26])=[O:25])(=[O:16])=[O:17])[C:8](=[O:14])[O:9]2)[CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 86694360HCID 86694360, compound

Product 1

HCID 86694359HCID 86694359, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl (1R*,2S*,5S*)-6-oxabicyclo[3.1.0]hexan-2-yl((2-nitrophenyl)sulfonyl)-carbamate (2.0 g, 5.10 mmol) in MeOH (40 mL) was added Amberlyst 15 (4.0 g) and the resulting suspension was stirred for 1.5 h at 25° C. The reaction mixture was filtered and concentrated. The title compound was obtained after purification by flash chromatography (heptane-EtOAc 90:10→EtOAc) as a beige solid (1.24 g, 73%): TLC (heptane/EtOAc 1:2) Rf=0.36; tR=0.80 min (UPLC 1), tR, 0.77 min (LC-MS 3); ESI-MS: 346 [M+NH4]+ (LC-MS 3).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa7d2811c324a7a96ae752f034cc431
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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