4-Toluenesulfonyl chloride → 4-{4-[(2S)-2-tert-Butoxycarbonyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-butyric acid ethyl ester

HRID 1250870Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

411 mg of 4-[4-((2S)-2-amino-2-tert-butoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester were dissolved in 10 ml of anhydrous DMF and cooled to 0° C. 191 mg of 4-toluenesulfonyl chloride and 0.34 ml of diisopropylethylamine were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and the solvents removed in vacuo. The residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1). Yield 295 mg. MS (ES+): m/e=506.2 (M+H)+; 450.2.

Workup

filtrationThe reaction mixture was filtered
customthe solvents removed in vacuo
customThe residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1)

Sources & evidence

ORD record: ord-6bc302295ade406ebea770fb217434c6
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06340679B1

Reaction notes

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