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Triethylamine → 1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

HRID 1979482
Notes
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Reaction equation

HRID 1979482 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[C:25]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:35])[C:26]1[CH:34]=[CH:33][CH:32]=[C:28](C([O-])=O)[CH:27]=1.C(C(C[N:51]1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]2)[CH2:54][CH:53]([NH2:68])[C:52]1=[O:69])=O)(C)(C)C>O1CCCC1>[O:69]=[C:52]1[NH:51][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67]2)[CH2:54][CH:53]1[NH:68][C:23]([NH:20][C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35])[CH:27]=1)=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 154908351-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 184201251,3-Benzenedicarboxylic acid, mono(phenylmethyl) ester

Product 1

HCID 212018741-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea
Yield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Diphenylphosphoryl azide (938 mg) and triethylamine (354 mg) were added to a solution of monobenzyl isophthalate (874 mg) in anhydrous tetrahydrofuran (30 ml), the mixture was stirred at 100° C. for one hour and 30 minutes. The resultant mixture was allowed to cool, 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (680 mg) was added thereto, the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to thereby obtain 890 mg of the title compound.

Workup

  1. temperatureto cool
  2. stirringthe mixture was stirred at room temperature for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-d3a24068c3ab4c7899dd0dd5280dceac
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239131B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes