1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl(2S,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

HRID 1486033Notes

Reaction equation

HRID 1486033 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C@@H:9]([CH3:22])[C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](O)=[O:12].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:18]([O:17][C:15](=[O:16])[NH:14][C@H:10]1[C@H:9]([CH3:22])[NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:11]1=[O:12])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90079354(2S,3S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-butyric acid

Product 1

HCID 90082343tert-butyl(2S,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-butyric acid (5.29 g, 17.1 mmol) in N,N-dimethylformamide (50 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.26 g, 22.2 mmol) and the reaction was stirred at ambient temperature for 24 h. The mixture was concentrated in vacuo, diluted with water (100 ml) and extracted with ethyl acetate (2×100 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to give ((2S,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester which was used in the subsequent step without further purification (4.55 g, 91%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with water (100 ml)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d7232e912c74aab91b14163039ac11f
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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