Sodium Hydroxide → HCID 13749499, compound

HRID 2118870Notes

Reaction equation

HRID 2118870 reaction equation
O=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl.[NH2:17][C@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([CH2:25][C:26]([OH:28])=[O:27])[C:19]1=[O:29].C([BH3-])#N.[Na+]>O>[C:26]([CH2:25][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:18]([NH:17][CH:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:19]1=[O:29])([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 697322-Oxo-4-phenylbutyric acidHCID 5003444Sodium cyanoborohydrideHCID 18605799HCID 18605799, compound

Product 1

HCID 13749499HCID 13749499, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Suspend 4.45 g 2-oxo-4-phenylbutyric acid in 25 ml water and adjust the pH to 7 with 50% NaOH. Add 1.14 g 3-(S)-amino-1-carboxymethylperhydroazepin-2-one hydrochloride and again adjust the pH to 7 with 50% NaOH. Dilute the resulting solution with water to a total volume of 60 ml then add 0.943 g sodium cyanoborohydride. After 2 days at room temperature, add 50 ml Dowex 50 (H+) and stir the mixture for 1 hour. Extract the mixture with ether and then add the Dowex 50 and aqueous portion to the top of a 100 ml. column of Dowex 50 (H+). Elute first with water until the eluate is neutral and then with 2% pyridine in water until no further product elutes (ninhydrin detection). Concentrate the product containing fractions at aspirator pressure, redissolve the residue in 50 ml water and freeze dry. Isolate the 1-carboxymethyl-3-(S)-[(1 -carboxy-3-phenylpropyl)amino]perhydroazepin-2-one as a white hygroscopic solid.

Workup

  1. additionadd 50 ml Dowex 50 (H+)
  2. extractionExtract the mixture with ether
  3. additionadd the Dowex 50 and aqueous portion to the top of a 100 ml
  4. washElute first with water until the
  5. concentrationConcentrate the product
  6. additioncontaining fractions at aspirator pressure
  7. dissolutionredissolve the residue in 50 ml water
  8. customfreeze dry

Sources & evidence

ORD record
ord-a28af80293a6458e8f7caeff70b618f6
Source dataset
uspto-grants-1987_07
Patent number
US04680392

Reaction notes

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