1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67076730, compound

HRID 1055485Notes

Reaction equation

HRID 1055485 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[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>[F:22][C:18]1[C:3]2[O:4][CH2:5][C@H:6]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7](=[O:8])[NH:1][C:2]=2[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67076712HCID 67076712, compound

Product 1

HCID 67076730HCID 67076730, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-amino-6-fluorophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (2.6 g, 8.27 mmol) and EDCI (1.97 mg, 10.3 mmol) in DMF (40 mL) was stirred at RT for 6 h. The mixture was diluted with EtOAc and washed with H2O. The combined aqueous layers were extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the filtrate was concentrated to give a residue that was purified by silica gel chromatography to afford (S)-tert-butyl 9-fluoro-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (1.03 g, 42%) as an orange solid. MS m/z 319 (M+Na)+

Workup

  1. washwashed with H2O
  2. extractionThe combined aqueous layers were extracted with EtOAc
  3. dry with materialThe combined organic extracts 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-c2643667763e419b9a5ba1ca66e0e3b6
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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