Trifluoroacetic acid → HCID 90037481, compound

HRID 1055448Notes

Reaction equation

HRID 1055448 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[CH2:19][N:20]1[C:26](=[O:27])[C@@H:25]([NH:28]C(=O)OC(C)(C)C)[CH2:24][O:23][C:22]2[CH:36]=[CH:37][CH:38]=[CH:39][C:21]1=2>>[NH2:28][C@H:25]1[CH2:24][O:23][C:22]2[CH:36]=[CH:37][CH:38]=[CH:39][C:21]=2[N:20]([CH2:19][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][C:9]=2[CH3:8])[C:26]1=[O:27]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90037702HCID 90037702, compound

Product 1

HCID 90037481HCID 90037481, compoundYield 77.9%

Procedure

TFA (7.68 g, 67.3 mmol, Eq: 28.8) was added to a solution of (S)-tert-butyl 5-((2-methylnaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (1.01 g, 2.34 mmol, Eq: 1.00) and the mixture was stirred 2 h and the solvent removed. The residue was treated with sat. NaHCO3 and the aqueous mixture extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to afford (S)-3-amino-5-((2-methylnaphthalen-1-yl)methyl)-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one (606 mg, 76%) as a white foam.

Workup

  1. customthe solvent removed
  2. additionThe residue was treated with sat. NaHCO3
  3. extractionthe aqueous mixture extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-999e2dc4c31144eba453247233f49fcb
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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