Triphenylphosphine → HCID 69999615, compound

HRID 1634054Notes

Reaction equation

HRID 1634054 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:54])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]([C:39](=[O:53])[C:40]1[CH:45]=[C:44]([NH:46][C:47](=[O:49])[CH3:48])[CH:43]=[CH:42][C:41]=1[N:50]=[N+]=[N-])[CH2:29][C:30](=[O:38])NC1CCCCC1>ClCCCl>[CH3:20][O:21][C:22](=[O:54])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:39](=[O:53])[C:40]2[CH:45]=[C:44]([NH:46][C:47](=[O:49])[CH3:48])[CH:43]=[CH:42][C:41]=2[NH:50][C:30](=[O:38])[CH2:29]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86758784HCID 86758784, compound

Product 1

HCID 69999615HCID 69999615, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

500 mg polymerbound triphenylphosphine (Fluka #93093) was added to 267 mg (0.55 mmol) 6-{(5-acetylamino-2-azido-benzoyl)-cyclohexylcarbamoylmethyl-amino}-hexanoic acid methyl ester in 8 ml 1,2-dichloroethane. The suspension was heated to 50° C. for 120 min and the solvent was filtered off. The solid was collected, suspended in a solution consisting of 8 ml AcOH, 1 ml water, and 1 ml dioxane and the mixture was heated to reflux for 24 h and filtered. The filtrate was concentrated in vacuo and the residue flashchromatographed on silicagel in EtOAc/hexane as eluent to yield 6-(7-acetylamino-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-hexanoic acid methyl ester (117 mg, 0.32 mmol): MS (ISP) 362(M+H)+.

Workup

  1. filtrationthe solvent was filtered off
  2. customThe solid was collected
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 24 h
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8dad46c194d0469eac93c3f9a34ec5a4
Source dataset
uspto-grants-2003_01
Patent number
US06506744B1

Reaction notes

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