Water → HCID 68867115, compound

HRID 1988250Notes

Reaction equation

HRID 1988250 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:17][NH2:18])=[CH:11][C:10]=1[C:30]([CH3:33])([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH2:17][NH:18][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:11][C:10]=1[C:30]([CH3:33])([CH3:32])[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 17819215HCID 17819215, compound

Product 1

HCID 68867115HCID 68867115, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-benzyloxy-3-tert-butylphenyl)-2-benzyloxycarbonylaminopropylamine (1.27 g, 2.84 mmol) in methylene chloride (29 ml), TEA (0.6 ml, 4.26 mmol) and then methanesulfonyl chloride.(0.3 ml, 3.69 mmol) were added slowly under cooling with ice. After stirring for 30 min., the mixture was mixed with water and extracted with chloroform. The organic layer was dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:ethyl acetate:n-hexane=1:1:2), giving the titled compound (1.23 g, 83%).

Workup

  1. addition(0.3 ml, 3.69 mmol) were added slowly
  2. temperatureunder cooling with ice
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a343d9b6fa0744d6ab73891c3812b88f
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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