Dimethyl Sulfoxide → HCID 59656414, compound

HRID 1726504Notes

Reaction equation

HRID 1726504 reaction equation
CS(C)=O.[CH2:5]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH:30]([OH:32])[CH3:31])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:12][CH2:11]1)=[O:9])[CH3:6].C(N(CC)CC)C>C(Cl)Cl>[CH2:5]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([C:30](=[O:32])[CH3:31])=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH2:12][CH2:11]1)=[O:9])[CH3:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 59656343HCID 59656343, compound

Product 1

HCID 59656414HCID 59656414, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of oxalyl dihcloride (85 mg, 0.665 mmol) in CH2Cl2 (10 mL) was added DMSO (104 mg, 1.33 mmol). After stirred at -78° C. for 10 min, a solution of 4-[4-(1-hydroxy-ethyl)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester 38 (180 mg, 0.443 mmol) in CH2Cl2 was added into the mixture by dropwise. The resultant mixture was stirred at −78° C. for another 30 min, then was added triethyl amine (224 mg, 2.22 mmol). The reaction mixture was warmed up to room temperature and stirred for 2 h. The resultant mixture was quenched with saturated ammonium chloride solution and the aqueous layer was extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product. The crude material was purified by Flash column chromatography (CH2Cl2: MeOH) to provide 45 mg of 4-(4-acetyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 39 in 25% yield. LC/MS showed m/z: 409 (M+H)+.

Workup

  1. temperatureThe reaction mixture was warmed up to room temperature
  2. stirringstirred for 2 h
  3. customThe resultant mixture was quenched with saturated ammonium chloride solution
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThe crude material was purified by Flash column chromatography (CH2Cl2: MeOH)

Sources & evidence

ORD record
ord-9b7fd6f63e284d6b8ab852bc764b8152
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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