Phenylacetyl isothiocyanate → HCID 59424567, compound

HRID 1711019Notes

Reaction equation

HRID 1711019 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[N:17]([CH2:18][O:19][CH3:20])[CH:16]=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[C:22]1([CH2:28][C:29]([N:31]=[C:32]=[S:33])=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:32]([NH:31][C:29](=[O:30])[CH2:28][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[S:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[N:17]([CH2:18][O:19][CH3:20])[CH:16]=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 59424634HCID 59424634, compound

Product 1

HCID 59424567HCID 59424567, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 245 (18 mg, 0.062 mmol) in THF (1 mL) was added 2-phenylacetyl isothiocyanate (12 mg, 0.069 mmol). The reaction mixture was stirred for 3 hours, concentrated under reduced pressure and the residue was purified by flash chromatography, eluent hexane/EtOAc (3:2) followed by recrystallization (MeCN/water), and preparative HPLC (Aquasil C-18, gradient: 60% MeOH to 95% MeOH in water), to afford title compound 246 (9.2 mg, 33% yield) as a white solid. 1HNMR: (CD3OD) δ (ppm): 8.35 (s, 1H), 8.03 (d, J=12.4 Hz, 1H), 7.96(d, J=3.13 Hz, 1H), 7.44-7.26 (m, 6H), 6.69 (d, J=3.13 Hz, 1H), 5.29 (quintuplet, J=6.65 Hz, 1H), 3.75 (s, 2H), 3.60 (d, J=10.96 Hz, 3H), 1.63(d, J=6.65 Hz, 6H). MS (m/z): 464.16 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by flash chromatography, eluent hexane/EtOAc (3:2)
  3. customfollowed by recrystallization (MeCN/water), and preparative HPLC (Aquasil C-18, gradient: 60% MeOH to 95% MeOH in water)

Sources & evidence

ORD record
ord-23b1f77e3fe54adf91c3d075e8414271
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

Loading…