Hydrochloric Acid → HCID 67497908, compound

HRID 1628333Notes

Reaction equation

HRID 1628333 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][N:14]3[C:17](=[O:34])[C@@H:18]([NH:26]C(=O)OC(C)(C)C)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[ClH:42]>ClCCl.CCOCC>[ClH:42].[NH2:26][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17]([N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:16]=2)[CH2:12][CH2:13]1)=[O:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 67497340HCID 67497340, compound

Product 1

HCID 67497908HCID 67497908, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The (S)-tert-butyl 1-(6-(4-fluorophenyl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (93.0 mg, 202 μmol) was dissolved in dichloromethane and TFA (1.0 mL, 13 mmol) was added. The resulting solution was stirred for three hours. The mixture was then concentrated and the residue was dissolved in ethyl acetate and extracted with saturated sodium bicarbonate (1×30 mL). The organic layer was then dried over magnesium sulfate and concentrated to dryness and the residue was again dissolved in ethyl acetate and 2.0 equivalents of 1M HCl in ether solution was added. A precipitate formed and the slurry was filtered and washed with hexanes to give (2S)-2-amino-1-(6-(4-fluorophenyl)indolin-1-yl)-3-phenylpropan-1-one hydrochloride (65 mg, 89% yield). MS ESI (pos.) m/e: 361.1 (M+H).

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionextracted with saturated sodium bicarbonate (1×30 mL)
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. dissolutionthe residue was again dissolved in ethyl acetate
  7. customA precipitate formed
  8. filtrationthe slurry was filtered
  9. washwashed with hexanes

Sources & evidence

ORD record
ord-b74ff71a4dbc4f85a458d8720217cd49
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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