Triethylamine → HCID 66864376, compound

HRID 1367188Notes

Reaction equation

HRID 1367188 reaction equation
C([S@@]([NH:7][C@H:8]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=1)[CH2:9][CH2:10][CH2:11][C:12](OCC)=[O:13])=O)(C)(C)C.C(N(CC)CC)C>CO>[F:24][C:19]1[CH:18]=[C:17]([C@H:8]2[NH:7][C:12](=[O:13])[CH2:11][CH2:10][CH2:9]2)[CH:22]=[C:21]([F:23])[CH:20]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 66865026HCID 66865026, compound

Product 1

HCID 66864376HCID 66864376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of ethyl (5S)-5-{[(S)-tert-butylsulfinyl]amino}-5-(3,5-difluorophenyl)pentanoate from Step A (4.42 g, 12.2 mmol) in MeOH (200 mL) was cooled to 0° C. Hydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 1 minute, after which time the reaction vessel was sealed and allowed to sit in the ice bath for 15 minutes. Dry nitrogen was then bubbled through the solution for 30 minutes, prior to removal of solvent in vacuo. More MeOH (˜50 mL) was added, and then removed in vacuo. After dissolving in a third volume of MeOH (100 mL), triethylamine (6.78 mL, 48.9 mmol) was introduced and the mixture was heated to 65° C. for 3 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between diethyl ether (100 mL) and 1 M HCl (50 mL). The organics were washed with additional 1 M HCl (50 mL), water (50 mL) and saturated brine (50 mL). The ethereal solution was dried over sodium sulfate, filtered and then concentrated in vacuo to provide the title compound, which could be used without further purification. MS: m/z=212 (M+1).

Workup

  1. customHydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 1 minute
  2. customafter which time the reaction vessel was sealed
  3. customDry nitrogen was then bubbled through the solution for 30 minutes
  4. customto removal of solvent in vacuo
  5. additionMore MeOH (˜50 mL) was added
  6. customremoved in vacuo
  7. additionwas introduced
  8. temperatureAfter cooling to ambient temperature
  9. customthe solvent was removed in vacuo
  10. customthe residue was partitioned between diethyl ether (100 mL) and 1 M HCl (50 mL)
  11. washThe organics were washed with additional 1 M HCl (50 mL), water (50 mL) and saturated brine (50 mL)
  12. dry with materialThe ethereal solution was dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cb1b83eaa744007aaadbfed7601ebdc
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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