Tetrahydrofuran → HCID 58009838, compound

HRID 1854324Notes

Reaction equation

HRID 1854324 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][C@@H:9]1[C@H:10]1[C@@H:12]2[CH:11]1[Si:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].[K+].C1C[O:26]CC1>>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:10]2[C@H:12]([CH:11]2[Si:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:13]([C:14]([OH:15])=[O:26])[CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 522689Potassium FluorideHCID 69013345HCID 69013345, compound

Product 1

HCID 58009838HCID 58009838, compoundYield 100%

Conditions

Temperature
60 °C

Procedure

A mixture of (1S,2R,4R,5R)-7-oxo-3-trimethylsilanyl-6-aza-tricyclo[3.2.1.0(2,4)]octane-6-carboxylic acid tert-butyl ester (1.7 g, 5.7 mmol) and potassium fluoride on alumina (2.10 g, 14.1 mmol) in THF (38 mL) was heated to about 60° C. for about 18 h. The mixture was cooled to ambient temperature and filtered through Celite®. The Celite® pad was rinsed with EtOAc (50 mL) and the filtrate was concentrated under reduced pressure to afford (1R,2S,4R,5R)-4-(tert -butoxycarbonylamino)-6-(trimethylsilyl)bicyclo[3.1.0]hexane-2-carboxylic acid (1.82 g, 100%): LC/MS (Table 2, Method a) Rt=2.62 min; MS m/z: 312 (M−H)−.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered through Celite®
  3. washThe Celite® pad was rinsed with EtOAc (50 mL)
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-17cdb53b62d2414ea58185ccb4e83d6a
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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