Phenylacetyl isothiocyanate → HCID 86604189, compound

HRID 1711026Notes

Reaction equation

HRID 1711026 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[NH:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[C:25]1([CH2:31][C:32]([N:34]=[C:35]=[S:36])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:35]([NH:34][C:32](=[O:33])[CH2:31][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[S:36])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[NH:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 59424696HCID 59424696, compound

Product 1

HCID 86604189HCID 86604189, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the 254 (26.8 mg, 0.84 mmol) in THF (1.6 ml) was added 2-phenylacetyl isothiocyanate (23 mg, 0.13 mmol). The mixture was stirred for 1 hr transferred onto a chromatography column and eluted sequentially with EtOAc/MeOH (9:1) and EtOAc/hexane (1:1), to afford title compound 255a (30 mg, 72% yield) as a white solid. 1HNMR: (DMSO-d6) δ (ppm): 12.65 (s, 1H), 12.43 (s, 1H), 11.79 (s, 1H), 8.31 (s, 1H), 8.06 (d, J=7.6 Hz, 2H), 7.91 (m, 1H), 7.52 (m, 4H), 7.43 (m, 1H), 7.34, (m, 4H), 7.27 (m, 1H), 7.18 (m, 1H), 3.83 (s, 2H). MS (m/z): 498.2 (M+1).

Workup

  1. washeluted sequentially with EtOAc/MeOH (9:1) and EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-ff1030b85c074dfebd7be78875041dc5
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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