Tripropylamine → 3-(3,3-Dibenzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-terahydro-1H-azepine-2-carboxylic acid

HRID 1759689Notes

Reaction equation

C([O:5][C:6]([CH:8]1[CH:14](C(O)=O)[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])(C)(C)C.C([N:32]([CH2:36]CC)CCC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH2:56]([NH:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>O1CCOCC1>[CH2:64]([N:63]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:36](=[O:46])[NH:32][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:10][N:9]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[CH:8]1[C:6]([OH:5])=[O:7])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

Conditions

Temperature: 75 °C

Procedure

The reaction is performed under an Argon blanket. 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (204 mg, 0.5 mmol) is dissolved in 10 ml dry Dioxane. Tripropylamine (94 μl, 0.5 mmol) is added and then Diphenyl phosphoryl azide (DPPA). The reaction is heated to 75° C. for 5 h. After cooling to room temperature, Dibenzylamine (190.6 μl, 1 mmol) is added via syringe. The reaction is heated to 70° C. and stirred over night. Evaporation of the solvents and flash-chromatography, Hexane/Ethyl acetate (1:1) afforded the product: Cal. 606.8 found (M)+ 606.2.

Workup

temperatureAfter cooling to room temperature
temperatureThe reaction is heated to 70° C.
customEvaporation of the solvents and flash-chromatography, Hexane/Ethyl acetate (1:1)
customafforded the product

Sources & evidence

ORD record: ord-39772fbca4e6434ba996bc2fd06b0adb
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838454B2

Reaction notes

Loading…