HCID 22901516, compound → HCID 54247286, compound

HRID 2271033Notes

Reaction equation

HRID 2271033 reaction equation
C1C2C(COC([N:18]3[CH2:23][CH2:22][N:21]([S:24]([C:27]4[S:28][C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:30][CH:31]=4)(=[O:26])=[O:25])[C@@H:20]([C:38]([NH:40][O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][O:43]4)=[O:39])[CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1>N1CCCCC1.CN(C=O)C>[C:32]1([C:29]2[S:28][C:27]([S:24]([N:21]3[CH2:22][CH2:23][NH:18][CH2:19][C@@H:20]3[C:38]([NH:40][O:41][CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)=[O:39])(=[O:25])=[O:26])=[CH:31][CH:30]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 1

HCID 22901516HCID 22901516, compound

Product 1

HCID 54247286HCID 54247286, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

(2R)-4-(9-Fluorenylmethyloxycarbonyl)-1-(5-phenylthiophene-2-sulfonyl)-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (16.5 g) was dissolved in a solution (160 ml) of 20% piperidine in DMF at room temperature. After stirring for 30 minutes at said temperature, the solution was concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: 1% MeOH in CHCl3, then 4% MeOH in CHCl3) to give 9.57 g of (2R)-1-(5-phenylthiophene-2-sulfonyl)-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide as an amorphous powder.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was purified by SiO2 column chromatography (eluent

Sources & evidence

ORD record
ord-3d775cc1bcbf4828b1259edf5c3cc65f
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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