Triethylamine → HCID 67494711, compound

HRID 1620379Notes

Reaction equation

HRID 1620379 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:26][CH2:27][C@H:28]([N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:29]([O:31][CH3:32])=[O:30]>ClCCl>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:26][CH2:27][C@H:28]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:29]([O:31][CH3:32])=[O:30])(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 67494636HCID 67494636, compound

Product 1

HCID 67494711HCID 67494711, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.2 ml (8.5 mmol) of triethylamine and then 800 mg (2.8 mmol) of 4-benzyloxybenzenesulfonyl chloride in 8 ml of dichloromethane are added to a solution of 670 mg (2.6 mmol) of methyl(S)-3-amino-2-piperidin-1-ylpropanoate in 10 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 18 h, hydrolyzed and then diluted with dichloromethane. The product is extracted with dichloromethane. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 940 mg (85%) of methyl(S)-3-(4-benzyloxybenzenesulfonylamino)-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Workup

  1. extractionThe product is extracted with dichloromethane
  2. washThe organic phase is washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-e95fa1a7f3bd4f2e9cdf5e6180e2699a
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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