Hydrochloric Acid → HCID 58840800, compound

HRID 1268758Notes

Reaction equation

HRID 1268758 reaction equation
C([O:5][C@H:6]1[CH2:18][N:9]2[C@@H:10](C(Cl)(Cl)Cl)[O:11][C:12](=[O:13])[C@:8]2([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)[CH2:7]1)(C)(C)C.Cl>CO.C(OCC)C>[Br:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@@:8]2([C:12]([O:11][CH3:10])=[O:13])[CH2:7][C@@H:6]([OH:5])[CH2:18][NH:9]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58840789HCID 58840789, compound

Product 1

HCID 58840800HCID 58840800, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of (3R,6R,7aS)-6-tert-butoxy-7a-(4-Bromo-benzyl)-3-(trichloromethyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-1-one (0.4 g) (Prep. 2) in 10 mL of MeOH was added 1 mL of dry HCl in ethyl ether, and the resulting solution was refluxed for 13 hrs. The MeOH was evaporated, and the residue dissolved in DCM and washed with aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure to afford the above-titled compound (0.170 g). 1H NMR (CDCl3): 7.40 (2H,d), 7.05 (2H,d), 4.25 (1H, m), 3.65 (3H,s), 3.15 (1H,d), 2.85–3.0 (2H,m), 2.45–2.6 (2H,m), 1.85 (1H,dd).

Workup

  1. temperaturethe resulting solution was refluxed for 13 hrs
  2. customThe MeOH was evaporated
  3. dissolutionthe residue dissolved in DCM
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-12340bbe6c1b467784872eba4c246a9f
Source dataset
uspto-grants-2007_04
Patent number
US07199125B2

Reaction notes

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