4-Toluenesulfonyl chloride → Acetic acid (S)-2-tert-butoxycarbonylamino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butyl ester

HRID 1455586Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:32][CH3:33])[C@H:10]([O:28][C:29](=[O:31])[CH3:30])[C:11]([NH:13][NH:14][C:15](=[O:27])[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:32][CH3:33])[C@H:10]([O:28][C:29](=[O:31])[CH3:30])[C:11]1[O:27][C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:26])[F:25])=[CH:18][CH:17]=2)=[N:14][N:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

acetic acid (S)-2-tert-butoxycarbonylamino-1-[N′-(4-trifluoromethoxy-benzoyl)-hydrazinocarbonyl]-butyl ester (0.21 mmol, 0.1 g) is dissolved in THF (5 mL) and the solution filled into a Smith Microwave synthesizer reaction vessel. 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,2,3-diazaphosphorine on polystyrene (1.05 mmol, 0.456 g, 2.3 mmol/g loading) and the p-Toluenesulfonic chloride (0.25 mmol, 0.048 g) are added and the reaction mixture heated at 150° C. for 10 min (fixed hold time) in the microwave synthesizer.

Workup

additionthe solution filled into a Smith Microwave synthesizer reaction vessel

Sources & evidence

ORD record: ord-e2e5684c189747eb8283e9b58c2d4bcd
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482448B2

Reaction notes

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