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

HRID 1759689
Notes
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Reaction equation

HRID 1759689 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7616TripropylamineHCID 7656DibenzylamineHCID 199401P,P-Diphenylphosphinic azideHCID 155505231-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester

Product 1

HCID 120878673-(3,3-Dibenzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-terahydro-1H-azepine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction is heated to 70° C.
  3. customEvaporation of the solvents and flash-chromatography, Hexane/Ethyl acetate (1:1)
  4. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes