Hydrochloric Acid → HCID 71766272, compound

HRID 76329Notes

Reaction equation

HRID 76329 reaction equation
[BH4-].[Na+].C(O)(=O)C(O)=O.[C:9]([CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=1[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27](OCC)=[O:28])#[N:10].CO.Cl>C1COCC1.O.ClCCl>[OH:28][CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:13]1[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=1[CH2:11][C:9]#[N:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 86698213HCID 86698213, compound

Product 1

HCID 71766272HCID 71766272, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 10.8 g of NaBH4 (284 mmol, 11 eq.) in 110 mL of THF there is added, at several points over a period of time, ethyl N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-β-alaninate oxalate (10.6 g, 25.9 mmol). Stirring is carried out for 30 minutes at ambient temperature, and then 23.1 ml of methanol (570 mmol, 22 eq.) are poured in dropwise. The mixture is heated for 16 hours at 60° C., and is then hydrolysed using 100 mL of 5N hydrochloric acid. There are then added 100 mL of dichloromethane and 200 mL of demineralised water. After separation of the phases, 50 ml of 10N sodium hydroxide solution are added (pH>10) to the aqueous phase and extraction is carried out using 3×70 mL of dichloromethane. The organic phases are combined and washed with 2×75 mL of saturated aqueous NaCl solution and then dried over MgSO4. After carrying out drying in vacuo, there are obtained 6.15 g of a colourless oil corresponding to the title compound.

Workup

  1. customAfter separation of the phases, 50 ml of 10N sodium hydroxide solution
  2. additionare added (pH>10)
  3. extractionto the aqueous phase and extraction
  4. washwashed with 2×75 mL of saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. customAfter carrying out drying in vacuo, there

Sources & evidence

ORD record
ord-cd8f73b22f9042e89c2260e0a77c5840
Source dataset
uspto-grants-2014_09
Patent number
US08835627B2

Reaction notes

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