Lawesson's reagent → 1,1-dimethylethyl 7-{3-[(phenylmethyl)amino]-3-thioxopropanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 473862Notes

Reaction equation

O=[C:2]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=2[CH:23]=1)=[O:5].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>O1CCOCC1>[C:26]1([CH2:25][NH:24][C:2](=[S:41])[CH2:3][C:4]([C:6]2[CH:7]=[CH:8][C:9]3[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=3[CH:23]=2)=[O:5])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1,1-dimethylethyl 7-{3-oxo-3-[(phenylmethyl)amino]propanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (180 mg, 0.42 mmol) and Lawesson's reagent (177 mg, 0.44 mmol) in 1,4-dioxane (2 mL) was stirred at 65° C. for two hours. The reaction mixture was cooled and purified directly by silica gel chromatography (25% ethyl acetate in hexanes) to give 1,1-dimethylethyl 7-{3-[(phenylmethyl)amino]-3-thioxopropanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (155 mg, 83% yield). MS (EI) for C24H28N2O4S: 441 (MH+).

Workup

temperatureThe reaction mixture was cooled
custompurified directly by silica gel chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d630eb7f37c24599b555929a0ca62670
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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