Hydrochloric Acid → HCID 13243541, compound

HRID 482757Notes

Reaction equation

HRID 482757 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([CH:14]([C:16]([OH:18])=[O:17])[CH3:15])[C:4]1=[O:19].[CH2:20]([CH2:27][C:28](=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([BH3-])#N.[Na+].Cl>C(O)(=O)C.CO>[ClH:1].[C:16]([CH:14]([N:5]1[C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH2:8][CH2:9][CH:3]([NH:2][CH:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:4]1=[O:19])[CH3:15])([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 13243543HCID 13243543, compound

Product 1

HCID 13243541HCID 13243541, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A solution of 3-amino-1-(1-carboxyethyl)-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one hydrochloride (3 g) and ethyl benzylpyruvate (6.5 g) in acetic acid (30 ml) and methanol (30 ml) was stirred at room temperature for 1 hour. Sodium cyanoborohydride (0.8 g) in methanol (10 ml) was added over 4 hours. The reaction mixture was stirred at room temperature for 24 hours. Cencentrated hydrochloric acid (2 ml) was added and the mixture was stirred for 1 hour. The solvents were removed at reduced pressure and the residue was partitioned between water (50 ml) and ether (30 ml). The pH was adjusted to 9.4, the ether layer was separated and discarded. The aqueous solution was adjusted to pH 4.3 and extracted with ethyl acetate (3×50 ml). The combined ethyl acetate solutions were dried over magnesium sulfate and the solvent removed under reduced pressure. Hydrogen chloride was bubbled into a solution of the crude product in methylene chloride (10 ml) for 2 minutes. The solution was evaporated to give 1-(1-carboxyethyl)-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one hydrochloride, as a mixture of diastereomers, m.p. 87°-94°.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe solvents were removed at reduced pressure
  3. customthe residue was partitioned between water (50 ml) and ether (30 ml)
  4. customthe ether layer was separated
  5. extractionextracted with ethyl acetate (3×50 ml)
  6. dry with materialThe combined ethyl acetate solutions were dried over magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. customHydrogen chloride was bubbled into a solution of the crude product in methylene chloride (10 ml) for 2 minutes
  9. customThe solution was evaporated

Sources & evidence

ORD record
ord-977bddfc6f6842f6b5979e9aedbf4a54
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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