Water → HCID 69142608, compound

HRID 1794072Notes

Reaction equation

HRID 1794072 reaction equation
C1C2C(COC([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[CH:30][CH:29]=4)=[O:25])[CH2:20][CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.O>N1CCOCC1>[CH2:35]([O:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][O:26][C:24]([N:21]2[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]2)=[O:25])=[CH:33][CH:32]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 962WaterHCID 69140720HCID 69140720, compound

Product 1

HCID 69142608HCID 69142608, compound

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

A solution of 274 mg (0.5 mmol) piperazine-1,4-dicarboxylic acid 4-benzyloxy-benzyl ester 9H-fluoren-9-ylmethyl ester in 13 ml morpholine was stirred at rt for 1 h. Then 23 ml of chilled water was added, the suspension filtered and the filtrate extracted with TBME. The organic layer was washed with water, brine, dried over Na2SO4 and evaporated: 54 mg piperazine-1-carboxylic acid 4-benzyloxy-benzyl ester as light yellow, waxy solid. MIR: 3300 cm−1, 1688 cm−1. 1H-NMR (CDCl3): 1.77 br, 1H; 2.75–2.90 m, 4H and 3.40–3.50 m, 4H; 5.06 s and 5.07 s, 4H; 6.96 d, J=8.8 Hz, 2H and 7.28–7.44 m, 7H. MS (ISP): 327.3 (M+H)+.

Workup

  1. filtrationthe suspension filtered
  2. extractionthe filtrate extracted with TBME
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custom5.06 s and 5.07 s, 4H
  7. custom6.96 d, J=8.8 Hz, 2H and 7.28–7.44 m, 7H

Sources & evidence

ORD record
ord-8952efa008f04fafa8714080669acf46
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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