Hydrochloric Acid → HCID 68427487, compound

HRID 1785615Notes

Reaction equation

HRID 1785615 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:13][C:14](=O)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]([NH2:12])=O)=[CH:5][CH:4]=1.CSC.B.Cl.[OH-].[Na+]>C1COCC1.O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:10][NH2:12])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 68425957HCID 68425957, compound

Product 1

HCID 68427487HCID 68427487, compoundYield 104.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(R)-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)-acetylamino]-acetamide (316 g, 0.96 mol) in THF (2 L) is heated to 35° C. and borane dimethyl sulfide (428 mL, 4.28 mol) is added over approximately 1 hour after which the reaction is heated to reflux for 18 hours. After cooling the reaction solution to 8° C. sufficient 3N HCl (approx. 400 mL) is added until the pH of the solution is approximately 1. The reaction solution is then heated to reflux for 1 hour. The reaction is then cooled and the pH adjusted to 8 by the slow addition of 25% aqueous NaOH (300 mL). The entire reaction solution is poured into a vessel containing a mixture of CH2Cl2 (3 L) and water (1.5 L). The organic layer is decanted and the water layer treated with CH2Cl2 (1.5 L). The organic layers are combined, washed with brine (2.5 L) then dried over Na2SO4. The solvent in removed in vacuo to afford 302 g (quantitative yield) of the desired product as an amber colored oil.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 18 hours
  3. additionis added until the pH of the solution
  4. temperatureThe reaction solution is then heated
  5. temperatureto reflux for 1 hour
  6. temperatureThe reaction is then cooled
  7. additionThe entire reaction solution is poured into a vessel
  8. additioncontaining
  9. customThe organic layer is decanted
  10. additionthe water layer treated with CH2Cl2 (1.5 L)
  11. washwashed with brine (2.5 L)
  12. dry with materialthen dried over Na2SO4
  13. customThe solvent in removed in vacuo

Sources & evidence

ORD record
ord-efd2d005c4974fceb69e34e9a02f044a
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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