1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-tert-Butyl 4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate

HRID 1055421Notes

Reaction equation

HRID 1055421 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[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>[O:8]=[C:7]1[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[C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=[CH:21][C:2]=2[NH:1]1

Participants

5

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 21091528(S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

Product 1

HCID 67077046(S)-tert-Butyl 4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamateYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (1.23 g, 3.38 mmol) and EDCI (803 mg, 4.19 mmol) in DMF (25 mL) was stirred at RT for 6 h, diluted with EtOAc and washed with H2O. The combined aqueous washes were extracted with EtOAc and the combined organic solutions were dried over MgSO4, filtered. The filtrate was concentrated to give a residue that was purified by silica gel chromatography to afford the title compound (1.04 g, 89%) as a light brown oil. MS m/z 369 (M+Na)+

Workup

  1. washwashed with H2O
  2. extractionThe combined aqueous washes were extracted with EtOAc
  3. dry with materialthe combined organic solutions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give a residue that
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-bcff59f9e1d34f8b8f58a662159fbaae
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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