Hydrochloric Acid → HCID 18653158, compound

HRID 2253628Notes

Reaction equation

HRID 2253628 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.Cl.[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH:35]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:34]1.Cl>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[C:1]([NH:11][C@H:12]([C:16]([CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH:35]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:34]1)=[O:18])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 726987N-Carbobenzoxy-L-valineHCID 6603637ethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

Product 1

HCID 18653158HCID 18653158, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

CBZ-L-Valine (12.6 g, 0.05 mol) and triethylamine (5.06 g 0.05 mol) were dissolved in THF (100 mL) and then cooled to 0°-5° C, with an ice water bath. Ethyl chloroformate (5.44 g, 0.05 mol) in THF (35 mL) was added dropwise at 0°-5° C. Following the addition the mixture was stirred for one hour in the cold. Ethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (14.5 g, 0.06 mol) and triethylamine (6.1 g, 0.06 mol) in CH2Cl2 (60 mL) and THF (30 mL) were added at 0° C. The reaction mixture as allowed to sit at room temperature overnight. Evaporation of the solvent yielded a viscous semisolid which was treated with ethyl acetate followed by 1N HCl and the layers were separated. The organic extract was washed with 1N aqueous HCl followed by 5% aqueous Na2CO3 and saturated aqueous NaCl-solution. After drying over MgSO4 , filtration and evaporation under reduced pressure afforded an oil (12.5 g) which was purified over silica gel using hexane: ethyl acetate (8:2) as eluent. Collected 2.9 g of the desired product as a viscous oil.

Workup

  1. temperaturecooled to 0°-5° C, with an ice water bath
  2. additionthe addition the mixture
  3. waitto sit at room temperature overnight
  4. customEvaporation of the solvent
  5. customyielded a viscous semisolid which
  6. customthe layers were separated
  7. extractionThe organic extract
  8. washwas washed with 1N aqueous HCl
  9. dry with materialAfter drying over MgSO4 , filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-05ac9d023c5b43b1b45c8fd0c7279caf
Source dataset
uspto-grants-1993_08
Patent number
US05232928

Reaction notes

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