Phenyl Isothiocyanate → HCID 178516744, compound

HRID 258107Notes

Reaction equation

HRID 258107 reaction equation
N[C@@H](CC1C=CC=CC=1)C(N[C@H:6]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[N:8]([CH2:23][C:24]2[NH:28][N:27]=[N:26][N:25]=2)[C:7]1=[O:29])=O.C(N(CC)CC)C.C1(N=C=S)C=CC=CC=1>O1CCCC1>[C:13]1([C:11]2[C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=3[N:8]([CH2:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)[C:7](=[O:29])[CH2:6][N:12]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 178511769HCID 178511769, compound

Product 1

HCID 178516744HCID 178516744, compoundYield 179.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3S)-3-[((2S)-2-amino-3phenylpropanoyl)amino]-1,3-dihydro-5-phenyl-1 -[(1H-tetrazol-5-yl)methyl]-2H-1,4-benzodiazepin-2-one (12 g) and triethylamine (3.83 ml) in tetrahydrofuran (240 ml) was added phenyl isothiocyanate (2.99 ml) at room temperature. After stirring for 4 hours at room temperature, the solvent of the reaction mixture was evaporated under reduced pressure. Hydrochloric acid was added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from ether to give (3S)-3-[[(2S)-2-[N'-phenyl)thioureido]-3-phenylpropanoyl]amino ]1,3-dihydro-5-phenyl-1-[(1H-tetrazol-5-yl)methyl]-2H-1,4-benzodiazepin-2-one (14.26 g).

Workup

  1. customthe solvent of the reaction mixture was evaporated under reduced pressure
  2. additionHydrochloric acid was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-684449740e23412c9b5cc4a2e4478e44
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

Loading…