1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-tert-butyl 8-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate

HRID 1055371Notes

Reaction equation

HRID 1055371 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](O)=[O:8].CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH3:22][C:19]1[CH:20]=[CH:21][C:2]2[NH:1][C:7](=[O:8])[C@@H:6]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][O:4][C:3]=2[CH:18]=1

Participants

5

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67076885(S)-3-(2-amino-5-methylphenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

Product 1

HCID 67076736(S)-tert-butyl 8-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamateYield 69.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(2-amino-5-methylphenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (3.85 g, 12.4 mmol, Eq: 1.00) and EDCI (2.38 g, 12.4 mmol, Eq: 1.00) were dissolved in DMF (50 mL) and the mixture was stirred at RT for 3 h. The mixture was diluted with EtOAc and washed with water, brine and the organic solution dried over Na2SO4. The mixture was filtered, concentrated and the residue was purified by silica gel chromatography to afford (S)-tert-butyl 8-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (2.51 g, 69%) as an off white foam.

Workup

  1. washwashed with water, brine
  2. dry with materialthe organic solution dried over Na2SO4
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-968648670f2d4eefa8e2f564e5891800
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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