Potassium Carbonate → HCID 71152424, compound

HRID 1497290Notes

Reaction equation

HRID 1497290 reaction equation
C([O:9][C@@H:10]1[C@H:15]2[N:16]([C:20](=[O:22])[CH3:21])[C:17](=[O:19])[O:18][C@H:14]2[CH2:13][C@H:12]([CH:23]([F:25])[F:24])[C@H:11]1[O:26]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[F:25][CH:23]([F:24])[C@@H:12]1[C@@H:11]([OH:26])[C@H:10]([OH:9])[C@H:15]2[NH:16][C:17](=[O:19])[O:18][C@H:14]2[CH2:13]1.[F:24][CH:23]([F:25])[C@H:12]1[CH2:13][C@H:14]([OH:18])[C@H:15]([NH:16][C:20](=[O:22])[CH3:21])[C@@H:10]([OH:9])[C@@H:11]1[OH:26]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 71152381HCID 71152381, compound

Product 2

HCID 71152424HCID 71152424, compoundYield 69%HCID 117856797HCID 117856797, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (3aS,4R,5R,6S,7aS)-3-acetyl-6-(difluoromethyl)-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (892 mg, 1.89 mmol) in MeOH (20 mL) was added K2CO3 (781 mg, 5.66 mmol). The mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was purified by SiO2 column, eluted with 5%-10% MeOH in DCM to give (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one (256 mg, 69%) and N-((1S,2R,3R,4S,6S)-4-(difluoromethyl)-2,3,6-trihydroxycyclohexyl)acetamide (176 mg, 31%), both were as a white solid. (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one: MS m/z 246.1 (M+23, 100%); 1H NMR (400 MHz, MeOD) δ 6.18 (td, J=56.6 Hz, 1.3 Hz, 1H), 4.74-4.78 (m, 1H), 3.51 (t, J=6.9 Hz, 1H), 3.30-3.38 (m, 2H), 2.25 (dt, J=15.4 Hz, 3.2 Hz, 1H), 2.01-2.16 (m, 1H), 1.82-1.90 (m, 1H). N-((1S,2R,3R,4S,6S)-4-(difluoromethyl)-2,3,6-trihydroxycyclohexyl)acetamide: MS m/z 240.1 (M+1, 100%); 1H NMR (400 MHz, MeOD) δ 5.98 (t, J=55.1 Hz, 1H), 3.89 (br s, 1H), 3.46-3.57 (m, 2H), 3.14-3.23 (m, 1H), 2.05-2.20 (m, 1H), 2.00 (s, 3H), 1.76 (dt, J=14.2 Hz, 3.6 Hz, 1H), 1.34-1.42 (m, 1H)

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by SiO2 column
  3. washeluted with 5%-10% MeOH in DCM

Sources & evidence

ORD record
ord-df809f42adaa47afb0a44b2a8373e547
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

Loading…