Acetic Acid → HCID 20446690, compound

HRID 2417853Notes

Reaction equation

HRID 2417853 reaction equation
N[CH:2]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1=[O:20].C(O)(=[O:23])C.N(OC(C)(C)C)=O.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[CH2:18]([O:17][C:15]([CH2:14][N:4]1[C:5]2=[CH:13][CH:12]=[CH:11][CH2:10][CH:6]2[CH2:7][CH2:8][CH2:9][C:2](=[O:23])[C:3]1=[O:20])=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 70297m-Chloroperbenzoic acidHCID 13491283HCID 13491283, compound

Product 1

HCID 20446690HCID 20446690, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-amino-1-ethoxycarbonylmethyl-3,4,5,6-tetrahydro-1-benzazocin-2-(1H)-one (8.0 g), acetic acid (0.4 ml), and t-butyl nitrite (4.2 ml) is dissolved in chloroform (150 ml) and the solution is refluxed for 2 hours then cooled to room temperature. m-Chloroperbenzoic acid (5.7 g) is added in portions, and the resulting solution stirred at room temperature for 30 minutes. The solution is washed with saturated aqueous sodium bicarbonate (120 ml), water (75 ml), 2N hydrochloric acid (50 ml), water (50 ml), 2N hydrochloric acid (50 ml), and water (50 ml). The solution is dried over magnesium sulfate and the solvent removed under reduced pressure to give 1-ethoxycarbonylmethyl-tetrahydro-1-benzazocin-2,3(1H)-dione.

Workup

  1. temperaturethe solution is refluxed for 2 hours
  2. washThe solution is washed with saturated aqueous sodium bicarbonate (120 ml), water (75 ml), 2N hydrochloric acid (50 ml), water (50 ml), 2N hydrochloric acid (50 ml), and water (50 ml)
  3. dry with materialThe solution is dried over magnesium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a91e153905cf492f83c1c708804c552f
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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