Benzene → HCID 69736425, compound

HRID 2304414Notes

Reaction equation

HRID 2304414 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[NH:5][C:6](=O)[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].P(Cl)(Cl)(Cl)(Cl)Cl.[NH:40]=[N+:41]=[N-:42].[CH:43]1C=CC=CC=1>>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([S:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:7]2[C:6]2[N:5]([C@:4]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)([CH3:43])[C:3]([OH:2])=[O:33])[N:42]=[N:41][N:40]=2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 241Benzene3×HCID 24530Hydrazoic acidHCID 24819Phosphorus pentachlorideHCID 18338285HCID 18338285, compound

Product 1

HCID 69736425HCID 69736425, compound

Procedure

N-(Toluene-4-sulfonyl-L-prolyl-(4-nitro)phenylalanine methyl ester was mixed with an equimolar amount of PCl5 in dry benzene and stirred for 90 minutes. The yellow solution was treated with a solution of hydrazoic acid in benzene and the mixture was stirred at room temperature for 2 hours, then it was diluted with benzene and washed with satd. NaHCO3 and brine. The organic layer was dried and evaporated to give a light yellow foam. The title compound was prepared from the product of the last reaction using standard basic hydrolysis techniques, yielding an off-white fluffy solid, mp 150-160° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. washwashed with satd
  3. customThe organic layer was dried
  4. customevaporated
  5. customto give a light yellow foam
  6. custombasic hydrolysis techniques
  7. customyielding an off-white fluffy solid, mp 150-160° C.

Sources & evidence

ORD record
ord-ab930d5799e24a2c92ece8355bdf3bf7
Source dataset
uspto-grants-2002_08
Patent number
US06436904B1

Reaction notes

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