Triethylamine → HCID 21948341, compound

HRID 2214817Notes

Reaction equation

HRID 2214817 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]([CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH2:30][C:29]2=[O:34])([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[CH:35]([C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1)=[CH2:36].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][C:18]([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([S:43]([C:40]3[CH:41]=[CH:42][C:37]([CH:35]=[CH2:36])=[CH:38][CH:39]=3)(=[O:45])=[O:44])[CH2:30][C:29]2=[O:34])([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][CH2:20]1)=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 9855777Styrene-4-sulfonyl chlorideHCID 21948286HCID 21948286, compound

Product 1

HCID 21948341HCID 21948341, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (735 mg) was added to a solution of 1-{[1-(tert-butoxycarbonyl)-4-ethoxycarbonylamino-4-piperidinyl]methyl}-2-piperazinone (1.4 g) in dichloromethane (80 ml), and 4-vinylbenzenesulfonyl chloride (885 mg) was added at 0° C., and the mixture was stirred at room temperature for 1 hour. An aqueous sodium carbonate solution was added to the reaction solution, and the mixture was extracted with dichloromethane, dried, concentrated, and purified by silica gel column chromatography (hexane:ethyl acetate=1:2) to obtain the colorless amorphous title compound (1.50 g).

Workup

  1. additionwas added at 0° C.
  2. extractionthe mixture was extracted with dichloromethane
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-f2061835cd94494bacb6f04f66b2b8a0
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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