HCID 69429842, compound → HCID 18448665, compound

HRID 1269463Notes

Reaction equation

HRID 1269463 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[CH:17]([NH:21][C:22](=[O:42])[CH2:23][CH:24]3[CH2:28][CH2:27][CH2:26][N:25]3[S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)(=[O:31])=[O:30])[CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=1)=[CH2:10])(C)(C)C>Cl.CCOC(C)=O>[NH2:7][CH2:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]([NH:21][C:22](=[O:42])[CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:39])[F:40])[CH:33]=1)(=[O:31])=[O:30])[CH2:16][CH2:15][CH2:14]2)=[CH2:10]

Participants

3

Reactant 1

HCID 69429842HCID 69429842, compound

Product 1

HCID 18448665HCID 18448665, compound

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A solution of [2-(5-{2-[1-(3-trifluoromethyl-benzenesulfonyl)-pyrrolidin-2-yl]-acetylamino}-5,6,7,8-tetrahydro-naphthalen-2-yl)-allyl]-carbamic acid tert-butyl ester (72 mg, 0.12 mmol) in saturated HCl/EtOAc (3 mL) was stirred at RT for 45 min. The solvent was removed with a rotary evaporator. The crude was diluted with saturated NaHCO3 (60 mL) and extracted with CH2Cl2 (60 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Reverse phase liquid chromatography [25–100% CH3CN (0.1% TFA)-H2O (0.1% TFA)] afforded the title compound-containing fractional collections. CH3CN was removed from the combined fractional collections with a rotary evaporator. The aqueous phase was neutralized with saturated with NaHCO3 (40 mL), extracted with CH2Cl2 (40 mL×3). The extract phase was washed with saturated with NaCl, dried over Na2SO4, filtered and concentrated. The title compound was obtained as an off-white solid. MS (ESI, pos. ion) m/z: 522 (M+1).

Workup

  1. customThe solvent was removed with a rotary evaporator
  2. additionThe crude was diluted with saturated NaHCO3 (60 mL)
  3. extractionextracted with CH2Cl2 (60 mL×3)
  4. washThe extract phase was washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customReverse phase liquid chromatography [25–100% CH3CN (0.1% TFA)-H2O (0.1% TFA)] afforded the title
  9. additioncompound-containing fractional collections
  10. customCH3CN was removed from the combined fractional collections with a rotary evaporator
  11. extractionextracted with CH2Cl2 (40 mL×3)
  12. washThe extract phase was washed with saturated with NaCl
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-31192b5c90d841a2b82d0ce8a29bad9f
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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