(S)-1-Boc-3-methylpiperazine → tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-6-yloxy)propyl]-3-methylpiperazinecarboxylate

HRID 22721Notes

Reaction equation

HRID 22721 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH3:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([O:25][CH2:26][CH:27]3[CH2:29][O:28]3)[CH:22]=[CH:21][C:19]=2[N:20]=1>C(O)C>[OH:28][C@H:27]([CH2:26][O:25][C:23]1[CH:22]=[CH:21][C:19]2[N:20]=[C:16]([CH3:15])[S:17][C:18]=2[CH:24]=1)[CH2:29][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]1[CH3:1]

Participants

4

Reactant 2

HCID 7023035(S)-1-Boc-3-methylpiperazineHCID 225916342-Methyl-6-(oxiran-2-ylmethoxy)benzothiazole

Product 1

HCID 86759596tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-6-yloxy)propyl]-3-methylpiperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of formula (B) was reacted with 2-methyl-6-(oxiran-2-ylmethoxy)benzothiazole (3 g, 7.3 mmol), a compound of formula (C), in ethanol. The reaction was refluxed for about 24 hours. When the reaction was substantially complete, the solvent was removed under reduced pressure, followed by preparative thin layer chromatography to render tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-6-yloxy)propyl]-3-methylpiperazinecarboxylate, a compound of formula (D).

Workup

  1. temperatureThe reaction was refluxed for about 24 hours
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-342833ffccb34641bf4a1d6b2ad4e828
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Reaction notes

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