Methanesulfonic Acid → HCID 89558366, compound

HRID 2402888Notes

Reaction equation

HRID 2402888 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[C:10](=[O:15])[O:11]2)=O)(C)(C)C.[CH3:16][S:17]([OH:20])(=[O:19])=[O:18]>C(OCC)(=O)C>[CH3:16][S:17]([O-:20])(=[O:19])=[O:18].[O:15]=[C:10]1[C@@H:9]2[CH2:14][C@@H:12]([CH2:13][NH2+:8]2)[O:11]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 11252852tert-Butyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Product 1

HCID 89558366HCID 89558366, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

(1S,4S)-3-Oxo-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid tert-butyl ester (100.0 g, 469 mmol) was dissolved in ethyl acetate (970 mL) and methanesulfonic acid (43.5 mL, 659 mmol) was added at 45° C. The mixture was stirred for 16 h at 45° C. The suspension was cooled to room temperature, filtered, and the precipitate was washed with ethyl acetate (240 mL) and dried in vacuo to yield the title compound as a white crystalline solid (94.2 g, 96%). MS (EI, neg): m/z=113 [cation-H]+, 69 [cation-H—CO2]+, 68 [cation-H—HCO2]+. 1H NMR (DMSO-d6, 600 MHz): δ 2.12 (dd, J=1.2 Hz, 12.0 Hz, 1H), 2.33 (s, 3H), 2.59 (d, J=12.0 Hz, 1H), 3.33 and 3.50 (ABX, JAB=12.0 Hz, JAX=1.9 Hz, JBX=0 Hz, each 1H), 4.58 (s, 1H), 5.41 (s, 1H), 9.74 (br s, 2H).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationfiltered
  3. washthe precipitate was washed with ethyl acetate (240 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0f98626eeb41493b95f76f45cac6d49c
Source dataset
uspto-grants-2014_08
Patent number
US08796471B2

Reaction notes

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