Trifluoroacetic acid → HCID 90038055, compound

HRID 1055490Notes

Reaction equation

HRID 1055490 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@H:10]([NH:26]C(=O)OC(C)(C)C)[C:11](=[O:25])[N:12]([CH2:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][C:15]=3[CH3:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[NH2:26][C@H:10]1[CH2:9][O:8][C:7]2[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=2[N:12]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]=2[CH3:24])[C:11]1=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90037237HCID 90037237, compound

Product 1

HCID 90038055HCID 90038055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to that described for Example 89 Step 2 except the reaction was stirred 45 min., (S)-tert-butyl 9-bromo-5-((2-methylnaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (40 mg, 78.2 μmol) in DCM (2 mL) was cooled to 0° C. and treated with TFA (300 μl). After 45 min, the mixture was concentrated to dryness and the residue azeotroped with MeCN to afford (S)-3-amino-9-bromo-5-((2-methylnaphthalen-1-yl)methyl)-2,3-dihydrobenzo[b][1,4]oxazepin-4 (5H)-one trifluoroacetate (41 mg), which was used without purification.

Workup

  1. waitAfter 45 min
  2. concentrationthe mixture was concentrated to dryness
  3. customthe residue azeotroped with MeCN

Sources & evidence

ORD record
ord-2129c75ec90d47298b6e672964ca5ec9
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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