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Trifluoroacetic acid → (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

HRID 403226
Notes
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Reaction equation

HRID 403226 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)[NH:10][C:11]2[CH2:12][O:13][CH2:14][C:15]([F:41])([F:40])[C@:16]([C:19]3[CH:24]=[C:23]([N:25]=C(C4C=CC=CC=4)C4C=CC=CC=4)[CH:22]=[CH:21][C:20]=3[F:39])([CH3:18])[N:17]=2)=CC=1.FC(F)(F)C(O)=O>ClCCl.O1CCOCC1.Cl>[NH2:25][C:23]1[CH:22]=[CH:21][C:20]([F:39])=[C:19]([C@:16]2([CH3:18])[C:15]([F:40])([F:41])[CH2:14][O:13][CH2:12][C:11]([NH2:10])=[N:17]2)[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86660407(R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Product 1

HCID 58562966(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent
HCID 6344
Dichloromethane
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of crude (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (1.2 mmol) in dichloromethane (20 ml) was added at 22° C. trifluoroacetic acid (2.6 ml) and stirring was continued for 1 h. The mixture was diluted with 1,4-dioxane (40 ml) and aqueous hydrochloric acid (1 M, 33 ml) and vigorous stirring of the emulsion at 22° C. was continued for 16 h. The mixture was evaporated and the residue partitioned between saturated aqueous NaCl and ethyl acetate, the aqueous layer was separated, the pH was adjusted to 14 using saturated aqueous Na2CO3 solution and extracted with ethyl acetate. The organic layer was dried, evaporated and the residue purified by chromatography on silica-NH2 using dichloromethane to give (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine as a colorless oil. MS (ISP): m/z=274.3 [M+H]+.

Workup

  1. stirringvigorous stirring of the emulsion at 22° C.
  2. waitwas continued for 16 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between saturated aqueous NaCl and ethyl acetate
  5. customthe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was dried
  8. customevaporated
  9. customthe residue purified by chromatography on silica-NH2

Sources & evidence

ORD record
ord-31b79d849e3943b6b50f48c48de30024
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748418B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes