4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid → 1-benzyl-4-(4-(benzyloxy)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide

HRID 1595649Notes

Reaction equation

HRID 1595649 reaction equation
C([O:3][C:4]([C:6]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C.C(OC1C=CC(S(C2(C(O)=O)CCN(CC3C=CC=CC=3)CC2)(=O)=O)=CC=1)C1C=CC=CC=1.[OH:69][NH:70]C(C1CCN(CC2C=CC=CC=2)C(S(C2C=CC(OCC3C=CC=CC=3)=CC=2)(=O)=O)C1)=O>CO.C1COCC1>[OH:69][NH:70][C:4]([C:6]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:11]1)=[O:3]

Participants

5

Reactant 3

HCID 109726574-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acidHCID 11123863HCID 11123863, compoundHCID 86757373HCID 86757373, compound

Product 1

HCID 99130531-benzyl-4-(4-(benzyloxy)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester (5.0 g, 10.1 mmol) was dissolved in MeOH/THF (1:1, 200 ml) and stirred at room temperature for 72 hrs. At the end reaction mixture was concentrated and the product was nuetralised with con. HCl by dissolving it in water (200 mL). After the neutralization reaction mixture was concentrated to dryness. Ice cold water (100 mL) was added to the solid and filtered. The product 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid was dried at 50° C. and taken to next step with out any purification. Colorless solid. MP: 66-68; Yield: 4.3 g, 91% ; MS: 466 (M+H) Starting from 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid (4.65 g, 10.0 mmol) and following the procedure outlined in example 83, 1.1 g of 4-(4-Benzyloxy-benzenesulfonyl-1-benzyl-piperidine-4-carboxylic acid hydroxyamide was isolated as a colurless solid. Yield 21%; mp 89° C.; MS: 481.1 1H NMR (300 MHz, DMSO-d6): δ2.27 (m, 3H), 2.76-2.79 (m, 2H), 3.43 (m, 4H),4.30 (s, 2H), 7.14-7.17 (d,2H), 7.50-7.73 (m, 5H), 9.37 (s, 1H), 10.53 (s, 1H), 11.18 (s, 1H).

Workup

  1. customAt the end reaction mixture
  2. concentrationwas concentrated
  3. dissolutionHCl by dissolving it in water (200 mL)
  4. customAfter the neutralization reaction mixture
  5. concentrationwas concentrated to dryness
  6. additionIce cold water (100 mL) was added to the solid
  7. filtrationfiltered
  8. dry with materialThe product 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid was dried at 50° C.
  9. customtaken to next step with out any purification
  10. customwas isolated as a colurless solid

Sources & evidence

ORD record
ord-a817b1226efd464db84d6d0d512d9652
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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