Hydrochloric Acid → HCID 68883845, compound

HRID 1269514Notes

Reaction equation

HRID 1269514 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[CH2:11]([O:18][C:19](=[O:36])[C:20]([CH3:35])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C@@H:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH:24]=1)[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].Cl[C:43]([O:45][CH3:46])=[O:44].Cl>C(Cl)Cl.O>[CH3:46][O:45][C:43]([N:31]1[CH2:32][CH2:33][CH2:34][C@@H:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([O:22][C:20]([C:19]([O:18][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:36])([CH3:21])[CH3:35])[CH:24]=2)[CH2:30]1)=[O:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 131726321HCID 131726321, compound

Product 1

HCID 68883845HCID 68883845, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

(S)-2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester-L-(+)-tartrate salt (Preparation 3, Method F; 119 mg, 0.24 mmol) was dissolved in 2 mL methlyene chloride and 1 mL water. Sodium bicarbonate (79 mg, 0.95 mmol) and methyl chloroformate (37 mL, 0.47 mmol) were added, and the biphasic mixture and resulting mixture stirred at ambient temperature for 2 h. The mixture was diluted with water (50 mL), acidified with 1N aqueous hydrochloric acid and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 90 mg (93%) of (S)-3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid methyl ester as a clear oil.

Workup

  1. customthe biphasic mixture and resulting mixture
  2. extractionextracted with diethyl ether (2×50 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab3b2bd2a45141e88141a5b710a9d78d
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

Loading…