Benzoyl isothiocyanate → HCID 86714332, compound

HRID 338100Notes

Reaction equation

HRID 338100 reaction equation
[NH2:1][C:2]1([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:6]([CH2:7][OH:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.[C:24]([N:32]=[C:33]=[S:34])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[C:24]([NH:32][C:33]([NH:1][C:2]1([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:6]([CH2:7][OH:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1)=[S:34])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86714333Benzyl 3-amino-4-(hydroxymethyl)-3-(2-thienyl)pyrrolidine-1-carboxylate

Product 1

HCID 86714332HCID 86714332, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzyl 3-amino-4-(hydroxymethyl)-3-(2-thienyl)pyrrolidine-1-carboxylate (21 g, 63 mmol) in tetrahydrofuran (210 mL) at 0° C. is treated with benzoyl isothiocyanate (8.95 mL, 66.3 mmol. The resulting solution is stirred for 2 hours at 0° C. and quenched by adding an aqueous solution of sodium chloride and methyl-t-butyl ether. The organic layer is separated, dried over magnesium sulfate, and the solvent evaporated to give the title compound (30 g, 95%). ES/MS (m/e): 496 (M+H).

Workup

  1. customquenched
  2. additionby adding an aqueous solution of sodium chloride and methyl-t-butyl ether
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-9d28441e75fb485ab27630829af51c08
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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