Triethylamine → HCID 21963993, compound

HRID 2212372Notes

Reaction equation

HRID 2212372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])[CH2:16][CH2:15][C:14]([CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])(O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.N12CCCN=C1CCCCC2>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])[CH2:16][CH2:15][C:14](=[CH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21963920HCID 21963920, compound

Product 1

HCID 21963993HCID 21963993, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The alcohol from the foregoing step (420 mg, 0.88 mmol) in dichloromethane (20 mL) was cooled to 0° C. under nitrogen and triethylamine (0.25 mL, 1.7 mmol) and methane sulfonyl chloride (0.1 mL, 1.3 mmol) were added. The reaction was stirred for 1 hour at 0° C. then further triethylamine (0.5 mL, 3.4 mmol) and methane sulfonyl chloride (0.21 mL, 2.7 mmol) added. After a further 30 minutes, the solution was washed with 2N aqueous hydrochloric acid (2×10 mL) and brine (10 mL), dried (MgSO4), evaporated and the residue taken up in tetrahydrofuran (20 mL). 1,8-diazabicyclo[5.4.0]undec-7-ene (0.26 mL, 1.7 mmol) was added and the mixture stirred for 5 minutes. Ethyl acetate (30 mL) was added, the solution washed with 1N aqueous sodium hydroxide (20 mL), and the aqueous layer extracted with further ethyl acetate (10 mL). The combined organic layers were washed with 2N aqueous hydrochloric acid (20 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave a residue which was purified by flash column chromatography on silica eluting with ethyl acetate:iso-hexane 1:1, to afford the desired product (196 mg).

Workup

  1. waitAfter a further 30 minutes
  2. washthe solution was washed with 2N aqueous hydrochloric acid (2×10 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. stirringthe mixture stirred for 5 minutes
  6. washthe solution washed with 1N aqueous sodium hydroxide (20 mL)
  7. extractionthe aqueous layer extracted with further ethyl acetate (10 mL)
  8. washThe combined organic layers were washed with 2N aqueous hydrochloric acid (20 mL) and brine (20 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customto leave a residue which
  12. customwas purified by flash column chromatography on silica eluting with ethyl acetate:iso-hexane 1:1

Sources & evidence

ORD record
ord-4a5d770ff514453cb64ecdb820d79bc2
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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