Succinic Acid → HCID 67519244, compound

HRID 1924441Notes

Reaction equation

HRID 1924441 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:21][C@H:22]3[NH:33][CH2:32][CH2:31][C@@:28]4([C:29]=2[CH:30]=1)[C@H:23]3[CH2:24][CH2:25][CH2:26][CH2:27]4)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[C:34]([OH:41])(=[O:40])[CH2:35][CH2:36][C:37]([OH:39])=[O:38]>CCOC(C)=O>[C:34]([OH:41])(=[O:40])[CH2:35][CH2:36][C:37]([OH:39])=[O:38].[C:8]([O:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:21][C@H:22]3[NH:33][CH2:32][CH2:31][C@@:28]4([C:29]=2[CH:30]=1)[C@H:23]3[CH2:24][CH2:25][CH2:26][CH2:27]4)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 67519268HCID 67519268, compound

Product 1

HCID 67519244HCID 67519244, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

(+)-(Morphinan-3-yloxy)methyl pivalate trifluoroacetic acid salt (240 mg, 0.509 mmol) from Example 62 was dissolved in EtOAc (20 mL) and washed with saturated NaHCO3 solution (20 mL×2). To the EtOAc layer was added succinic acid (60.1 mg, 0.509 mmol). The mixture was stirred at 40° C. for 10 min. and cooled to room temperature. The precipitated solution was filtered and washed with EtOAc (10 mL) to provide the title compound (243 mg, 100%) as a white solid.

Workup

  1. washwashed with saturated NaHCO3 solution (20 mL×2)
  2. temperaturecooled to room temperature
  3. filtrationThe precipitated solution was filtered
  4. washwashed with EtOAc (10 mL)

Sources & evidence

ORD record
ord-855a08f9aa354ccea72c36f0eed28257
Source dataset
uspto-grants-2012_05
Patent number
US08178551B2

Reaction notes

Loading…