Dichloromethane → (2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide

HRID 507296Notes

Reaction equation

HRID 507296 reaction equation
[NH2:1][C@@H:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:1][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([NH2:9])=[O:8])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73984-Chlorobenzenesulfonyl chlorideHCID 7271815(R)-2-Amino-4-methylpentanamide

Product 1

HCID 59001058(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above polymer-bound D-Leu-NH2 (20 g) was treated with CH2Cl2 (150 mL), pyridine (100 mL) and 4-chlorophenylsulfonyl chloride (20.0 g, 94.8 mmol). The mixture was shaken for 24 h, drained, washed with DMF (4×200 mL), CH2Cl2 (4×200 mL) and concentrated to give polymer-bound (R)-2-(4-chlorobenzenesulfonylamino)-4-methylpentanoic acid amide as a yellow resin (22 g). The completion of the reaction and the loading of the resin (0.57 mmol/g) were determined by the treatment of 50 mg of the resin with 10% (v/v) TFA/CH2Cl2 (2 mL) to give 8.7 mg of (R)-2-(4-chlorobenzenesulfonylamino)-4-methylpentanoic acid amide.

Workup

  1. washwashed with DMF (4×200 mL), CH2Cl2 (4×200 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-466db7542208430f8cdf772885ad7a2d
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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