Triethylamine → HCID 135456012, compound

HRID 635202Notes

Reaction equation

HRID 635202 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[NH:25][C:24](=[O:26])[C:23]2[C:18](=[C:19]([CH:27]([CH:29]([OH:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])[CH:20]=[CH:21][CH:22]=2)[N:17]=1)[CH2:7][CH3:8].C(N(CC)CC)C>C(Cl)Cl>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[NH:25][C:24](=[O:26])[C:23]2[C:18](=[C:19]([CH:27]([CH:29]([O:35][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])[CH:20]=[CH:21][CH:22]=2)[N:17]=1)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 135494392HCID 135494392, compound

Product 1

HCID 135456012HCID 135456012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.17 ml (2.17 mmoles) of methanesulfonyl chloride is added at 0° C. to 740 mg (1.81 mmoles) of the compound from Example 17 and 0.3 ml (2.17 mmoles) of triethylamine in 18 ml of absolute CH2Cl2. The mixture is allowed to come to room temperature and is stirred 30 minutes longer. The mixture is first extracted twice with 30 ml portions of 1 N NaOH and twice with 30-ml portions of 1 N HCl, the organic phase is dried over MgSO4, and the solvent is evaporated under vacuum in a rotary evaporator. The solid residue is stirred with a mixture of 30 ml ethyl acetate and 30 ml petroleum ether, and the product is filtered off. Yield: 650 mg (73.8%).

Workup

  1. customto come to room temperature
  2. extractionThe mixture is first extracted twice with 30 ml portions of 1 N NaOH and twice with 30-ml portions of 1 N HCl
  3. dry with materialthe organic phase is dried over MgSO4
  4. customthe solvent is evaporated under vacuum in a rotary evaporator
  5. stirringThe solid residue is stirred with a mixture of 30 ml ethyl acetate and 30 ml petroleum ether
  6. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-914228035c9e4977a4536bdbe0a7e23a
Source dataset
uspto-grants-2001_02
Patent number
US06187779B1

Reaction notes

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