Benzoyl isothiocyanate → Benzyl 1-(benzoylcarbamothioyl)-6a-(5-bromo-2-fluoro-phenyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

HRID 77571Notes

Reaction equation

HRID 77571 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([F:37])=[C:17]([C:19]23[CH2:26][N:25]([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH2:24][CH:23]2[CH2:22][O:21][NH:20]3)[CH:18]=1>O1CCCC1>[C:1]([NH:9][C:10]([N:20]1[C:19]2([C:17]3[CH:18]=[C:13]([Br:12])[CH:14]=[CH:15][C:16]=3[F:37])[CH2:26][N:25]([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[O:28])[CH2:24][CH:23]2[CH2:22][O:21]1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86762752Benzyl 6a-(5-bromo-2-fluoro-phenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

Product 1

HCID 86762753Benzyl 1-(benzoylcarbamothioyl)-6a-(5-bromo-2-fluoro-phenyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl isothiocyanate (2.87 mL, 21.28 mmol) is added drop wise to a solution of benzyl 6a-(5-bromo-2-fluoro-phenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (5.977 g, 14.2 mmol) in tetrahydrofuran (95 mL) and stirred overnight under nitrogen. The solvent is removed in vacuo. The crude product is purified over silica gel with a 30 minute 5% to 100% EtOAc in hexanes gradient to give the title compound (6.05 g, 73%). ES/MS (m/e): (79Br/81Br) 584/586 (M+H).

Workup

  1. customThe solvent is removed in vacuo
  2. customThe crude product is purified over silica gel with a 30 minute 5% to 100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-32c3773570f944749b77c4f2fb6e4b55
Source dataset
uspto-grants-2014_09
Patent number
US08841293B1

Reaction notes

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