Hydrochloric Acid → HCID 57624616, compound

HRID 1641537Notes

Reaction equation

HRID 1641537 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:16](OCC)=[O:17])[C:11](OCC)=[O:12])=[C:4]([Cl:29])[CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>C(O)C.O1CCCC1.O>[C:25]([O:24][C:22](=[O:23])[NH:21][C:10]([CH2:11][OH:12])([CH2:16][OH:17])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:29])([CH3:28])([CH3:26])[CH3:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 462028801,3-Diethyl 2-[2-(4-bromo-2-chlorophenyl)ethyl]-2-[[(1,1-dimethylethoxy)carbonyl]amino]propanedioate

Product 1

HCID 57624616HCID 57624616, compoundYield 97.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 2-[2-(4-bromo-2-chlorophenyl)ethyl]-2-[(tert-butoxycarbonyl)amino]malonate (217 g) of Reference Example 19 was dissolved in a mixed solution of ethanol (2170 mL), tetrahydrofuran (543 mL) and water (1085 mL), calcium chloride (97.7 g) was added at room temperature, and the mixture was stirred for 20 min. To the solution was added sodium borohydride (66.6 g) by portions at 0° C., and the mixture was stirred at the same temperature for 1 hr and further stirred at room temperature for 14 hr. 1M Hydrochloric acid (1085 mL) was added dropwise to the reaction mixture. The reaction solvent was evaporated under reduced pressure. 0.1M Hydrochloric acid (2713 mL) and ethyl acetate (3800 mL) were added to the residue. The organic layer was partitioned and extracted, and the extract was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (175 g) as white crystals.

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at the same temperature for 1 hr
  3. stirringfurther stirred at room temperature for 14 hr
  4. customThe reaction solvent was evaporated under reduced pressure
  5. addition0.1M Hydrochloric acid (2713 mL) and ethyl acetate (3800 mL) were added to the residue
  6. customThe organic layer was partitioned
  7. extractionextracted
  8. washthe extract was washed with 25% brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89ce5445591e4ef5b94b82b2be877706
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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