Hydrochloric Acid → HCID 20269007, compound

HRID 2417842Notes

Reaction equation

HRID 2417842 reaction equation
[Na].[NH2:2][CH:3]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]([CH2:16][C:17]([OH:19])=[O:18])[C:4]1=[O:20].[CH2:21]([CH2:28][C:29](=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+].Cl>C(O)(=O)C.CO>[C:17]([CH2:16][N:5]1[C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[CH2:8][CH2:9][CH2:10][CH2:11][CH:3]([NH:2][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:4]1=[O:20])([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 70093468HCID 70093468, compound

Product 1

HCID 20269007HCID 20269007, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A solution of 3-amino-1-carboxymethyl-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one sodium salt (13.2 g) and ethyl benzylpyruvate (30 g) in acetic acid (100 ml) and methanol (75 ml) is stirred at room temperature under an atmosphere of dry nitrogen for one hour. A solution of sodium cyanoborohydride (3.5 g) in methanol (30 ml) is then added dropwise during 4 hours. The reaction mixture is stirred at room temperature for 18 hours. Concentrated hydrochloric acid (10 ml) is added dropwise and the reaction mixture stirred at room temperature for 1 hour. The solvents are removed under reduced pressure and the residue partitioned between water (400 ml) and ether (100 ml). The pH is adjusted to 9 by the addition of 40% aqueous sodium hydroxide, and the ether layer is discarded. The pH of the aqueous phase is adjusted to 4.3 by the addition of concentrated hydrochloric acid, and the solution is extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts are combined and dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is dissolved in dichloromethane (150) (ml) and hydrogen chloride gas is bubbled in for five minutes. The solvent is evaporated and the residue is recrystallized to give 1-carboxymethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 1 hour
  2. customThe solvents are removed under reduced pressure
  3. customthe residue partitioned between water (400 ml) and ether (100 ml)
  4. additionThe pH is adjusted to 9 by the addition of 40% aqueous sodium hydroxide
  5. additionThe pH of the aqueous phase is adjusted to 4.3 by the addition of concentrated hydrochloric acid
  6. extractionthe solution is extracted with ethyl acetate (3×100 ml)
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent removed under reduced pressure
  9. dissolutionThe residue is dissolved in dichloromethane (150) (ml)
  10. customhydrogen chloride gas is bubbled in for five minutes
  11. customThe solvent is evaporated
  12. customthe residue is recrystallized

Sources & evidence

ORD record
ord-11e18867d9754fd595d0fb2d4fbae769
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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