Ethyl alpha-oxobenzenebutanoate → HCID 13749507, compound

HRID 1249264Notes

Reaction equation

HRID 1249264 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH:10]([C:12]([OH:14])=[O:13])[CH3:11])[C:4]1=[O:15].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.O=[C:35]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:36]([O:38]CC)=[O:37].C([BH3-])#N.[Na+]>O.C(O)C>[C:12]([CH:10]([N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:3]([NH:2][CH:35]([C:36]([OH:38])=[O:37])[CH2:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:4]1=[O:15])[CH3:11])([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 2723671Tetrabutylammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 18605807HCID 18605807, compound

Product 1

HCID 13749507HCID 13749507, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Dissolve 422 mg of 3-(S)-amino-1-(1-carboxyethyl)perhydroazepin-2-one hydrochloride in water and adjust the pH to 6.8 with 2M tetrabutylammonium hydroxide. Lyophilize the solution and dissolve the residue in 10 ml absolute ethanol. Add 1.98 g ethyl 2-oxo-4-phenylbutyrate and 7 g. powdered 4A molecular sieves. Add a solution of 357 mg. sodium cyanoborohydride in 3 ml absolute ethanol at a rate of 0.5 ml/hour. After the addition is complete, stir the reaction mixture overnight at room temperature. Filter the reaction mixture, wash the filter cake with ethanol and concentrate the combined filtrate and washings at aspirator pressure. Dissolve the residue in water and add 20 ml ether and 20 ml Dowex 50 (H+). Stir the mixture for 1 hour then draw off the ether layer.

Workup

  1. additionAdd a solution of 357 mg
  2. additionAfter the addition
  3. filtrationFilter the reaction mixture
  4. washwash the filter cake with ethanol
  5. concentrationconcentrate the combined filtrate and washings at aspirator pressure
  6. dissolutionDissolve the residue in water
  7. additionadd 20 ml ether and 20 ml Dowex 50 (H+)
  8. stirringStir the mixture for 1 hour

Sources & evidence

ORD record
ord-86233636b8094f34aeb7e1e13be8299b
Source dataset
uspto-grants-1986_12
Patent number
US04629787

Reaction notes

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