tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-6-yloxy)propyl]-3-methylpiperazinecarboxylate → (2S)-1-((2S)-2-methylpiperazinyl)-3-(2-methylbenzothiazol-6-yloxy)propan-2-ol

HRID 22722Notes

Reaction equation

HRID 22722 reaction equation
[OH:1][C@H:2]([CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:23]2[N:24]=[C:25]([CH3:27])[S:26][C:22]=2[CH:21]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C@@H:5]1[CH3:17]>FC(F)(F)C(O)=O>[CH3:17][C@H:5]1[CH2:6][NH:7][CH2:8][CH2:9][N:4]1[CH2:3][C@H:2]([OH:1])[CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:23]2[N:24]=[C:25]([CH3:27])[S:26][C:22]=2[CH:21]=1

Participants

3

Reactant 1

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

Product 1

HCID 69732419(2S)-1-((2S)-2-methylpiperazinyl)-3-(2-methylbenzothiazol-6-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-6-yloxy)propyl]-3-methylpiperazinecarboxylate (3 g) in trifluoroacetic acid (50 ml) was stirred at room temperature for 72 hours. The TFA was removed by evaporation under reduced pressure and the residue was dissolved in 50 ml of MEOH. The pH adjusted to between pH 8-pH 9 using tris-resin(Argonaut) rendering (2S)-1-((2S)-2-methylpiperazinyl)-3-(2-methylbenzothiazol-6-yloxy)propan-2-ol, which was used without further purification.

Workup

  1. customThe TFA was removed by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml of MEOH
  3. customwas used without further purification

Sources & evidence

ORD record
ord-2392ceadff7242c79652e66cd2c82ff6
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Reaction notes

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