1-Hydroxybenzotriazole → HCID 14515257, compound

HRID 648442Notes

Reaction equation

HRID 648442 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]2[CH2:19][CH2:20][N:21]=[C:3]12.[C:22]([NH:29][C@H:30]([C:38](O)=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(N(CC)CC)C>[C:25]([O:24][C:22]([NH:29][C@@H:30]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:38]([NH:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]2[CH2:19][CH2:20][N:21]=[C:3]12)=[O:39])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14515254HCID 14515254, compound

Product 1

HCID 14515257HCID 14515257, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Crude 4(R,S)-amino-2,4-dihydro-6-phenyl-1H-imidazo-[1,2-a]-[1,4]-benzodiazepine (1.37 g), Boc-L-phenyl-alanine (1.37 g, 5.17 mmole), 1-hydroxybenzotriazole (0.07 g, 5.17 mmole), and 1-ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride (0.99 g, 5.17 mmole) are combined in DMF (30 mL) and stirred at room temperature. The pH of the reaction mixture is adjusted to 8.5 with triethylamine, and after 1/2 hour, the DMF is removed in vacuo, and the residue partitioned between ethyl acetate and 10% citric acid solution (10 mL). The layers are separated and the organic phase is washed with sodium bicarbonate solution (NaHCO3, saturated). The combined organic layers are washed with brine, dried over Na2SO4, filtered, and evaporated to dryness in vacuo to give the title compound as a mixture of diastereomers.

Workup

  1. customthe DMF is removed in vacuo
  2. customthe residue partitioned between ethyl acetate and 10% citric acid solution (10 mL)
  3. customThe layers are separated
  4. washthe organic phase is washed with sodium bicarbonate solution (NaHCO3, saturated)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7a8698e845da4ada83c72bca6a34110c
Source dataset
uspto-grants-1988_04
Patent number
US04735941

Reaction notes

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