HCID 57047820, compound → HCID 21970189, compound

HRID 1872454Notes

Reaction equation

[CH3:1][O:2][C:3]([C@:5]1([N:16]=[N+:17]=[N-:18])[C@H:10]([OH:11])[CH2:9][C@@H:8]2[C@H:6]1[C@H:7]2[C:12]([O:14][CH3:15])=[O:13])=[O:4].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C@:5]1([N:16]=[N+:17]=[N-:18])[C:10](=[O:11])[CH2:9][C@@H:8]2[C@H:6]1[C@H:7]2[C:12]([O:14][CH3:15])=[O:13])=[O:4]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester (XII) (239 mg, 0.94 mmol) in DCM (6 mL) was added PCC (1.13 g, 2.62 mmol, 50% on silica gel) at 0° C. and the mixture was stirred at 23° C. for 2 d. The PCC was removed by filtration through a silica gel column and the pure (1S,2R,5R,6S)-2-azido-3-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic dimethyl ester (XIII) was obtained by silica gel column chromatography with hexane/EtOAc 2:1 as a white solid (152 mg, 64%). 1H-NMR (250 MHz, CDCl3) □1.64 (1H, t,J=3.4 Hz), 2.34 (1H, ddd,J=7.7, 5.5, 3.2 Hz), 2.46 (1H, dd,J=7.7, 3.1 Hz), 2.56 (1H, d,J=19.2 Hz), 3.06 (1H, dd, J=19.2, 5.5 Hz), 3.71 (3H, s), 3.89 (3H, s); MS[EI] 222 [(M-OCH3)+ ]; mp 62-65° C.;

Workup

customThe PCC was removed by filtration through a silica gel column

Sources & evidence

ORD record: ord-ecaab8e3a6ef4cd1931e6384b224921d
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107342

Reaction notes

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