Phenylmethanesulfonyl chloride → Methyl 2-[(4-{2-[(benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoate

HRID 2111986Notes

Reaction equation

HRID 2111986 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:7]([S:8]([NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:32][CH:33]=1)(=[O:10])=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68872919Methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride

Product 1

HCID 68869255Methyl 2-[(4-{2-[(benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoateYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alpha-toluenesulfonyl chloride (38 mg, 0.199 mmol) and methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride (64 mg, 0.199 mmol) were mixed in DCM (3 ml). PS-DIEA (3.66 mmol/g, 272 mg, 0.997 mmol) was added. The mixture was shaken at room temperature over a weekend. It was then loaded on a column (ISOLUTE® SI, 1 g/6 ml) and eluted with DCM. The product fractions were combined and evaporated. Oil product (17 mg) was obtained, yield 19%.

Workup

  1. washeluted with DCM
  2. customevaporated

Sources & evidence

ORD record
ord-106e18c00c604f85972168892eb228f4
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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