Triethylamine → 1-Ethyl-7-(3-hydroxy-propyl)-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione

HRID 68953Notes

Reaction equation

HRID 68953 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH2:19][CH2:20][C:21](O)=[O:22])[CH:17]=[CH:18][C:4]1=2)[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O.CO>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 66961114HCID 66961114, compound

Product 1

HCID 706568861-Ethyl-7-(3-hydroxy-propyl)-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dioneYield 74.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl)propionic acid (1.0 g) was dissolved in THF (20 ml) and was cooled to 0° C. in ice water bath. Triethylamine (0.525 ml) and ethyl chloroformate (0.325 ml) were added to this solution and stirred for 30 minutes at same temperature. Sodium borohydride (0.36 g) was added to the mixture under cooling in ice methanol bath. Methanol (0.64 ml) was added dropwise to the mixture and stirred for 1 hour at same temperature. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with magnesium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1). The purified product was condensed to dryness under reduced pressure to give the title compound (0.71 g) as a colorless oil.

Workup

  1. stirringstirred for 1 hour at same temperature
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. customcondensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-022e7504bb8d462495e98fd33af6d8c1
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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