Ethyl alpha-oxobenzenebutanoate → 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

HRID 1632774Notes

Reaction equation

HRID 1632774 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:3]1.O=[C:15]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:16]([CH:15]([NH:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:3]1)[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 133751543-Amino-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one

Product 1

HCID 204423383-[N-(1-carboethoxy-3-phenylpropyl)amino]-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

The 3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (0.250 g) is dissolved in 5 ml of methanol and 2.88 g of ethyl 2-oxo-4-phenylbutyrate is added. This is followed by the addition of a solution of 88 mg of sodium cyanoborohydride in 3 ml of methanol and 0.8 ml of glacial acetic acid. The reaction is stirred overnight under nitrogen and concentrated. The residue is dissolved in 20 ml of methylene chloride and washed with 10 ml of cold saturated sodium carbonate. After drying over magnesium sulfate the solution is concentrated to an oil which is purified by flash chromatography on silica gel [solvent, acetone, hexane (1:4)] to afford 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-2,3-dihydro-1,5-benzoxazepin-4(5H)-one; NMR (CDCl3) δ 9.35 (s (broad, 1], 6.50-7.30 (m, 10, 4.10 (q, 2), 2.67 (t (broad), 2], 1.21 (t, 3); IR (neat) 3220 (NH), 1730 (C=O, ester), 1685 (C=O, lactam) cm-1.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in 20 ml of methylene chloride
  3. washwashed with 10 ml of cold saturated sodium carbonate
  4. dry with materialAfter drying over magnesium sulfate the solution
  5. concentrationis concentrated to an oil which
  6. customis purified by flash chromatography on silica gel [solvent, acetone, hexane (1:4)]

Sources & evidence

ORD record
ord-b80d56e4f7ba4b28b0a55f85c26c429d
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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