Benzyl Alcohol → benzyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

HRID 1375356Notes

Reaction equation

HRID 1375356 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([OH:12])=[O:11])[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4](=[O:23])[CH2:3]1.[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC.CCOC(C)=O>C1(C)C=CC=CC=1>[O:1]=[C:2]1[N:8]([CH2:9][C:10]([O:12][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:11])[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4](=[O:23])[CH2:3]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 69427552(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetic acid

Product 1

HCID 86602390benzyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetic acid (8.0 g, 25.78 mM) and benzyl alcohol (3.35 g, 31 mM) were dissolved in 200 ml of toluene and 0.5 g of p-toluenesulfonic acid were added and resulting mixture was refluxed until TLC (Hexane/AcOEt 8/12) showed completion of reaction. Organic layer was washed 3 times with sodium bicarbonate solution, dried and toluene evaporated providing 9.5 g of product.

Workup

  1. customresulting mixture
  2. customcompletion of reaction
  3. washOrganic layer was washed 3 times with sodium bicarbonate solution
  4. customdried
  5. customtoluene evaporated

Sources & evidence

ORD record
ord-62f4f3f0b99a4184aa66847338d75331
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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