1-Hydroxybenzotriazole → HCID 22877895, compound

HRID 1488854Notes

Reaction equation

HRID 1488854 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C=CC2N(O)N=[N:33]C=2C=1.[NH:37]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][C:39](O)=[O:40]>CN(C)C=O.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:42]([NH:37][CH2:38][C:39]([NH2:33])=[O:40])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]

Participants

7

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9976854HCID 9976854, compound

Product 1

HCID 22877895HCID 22877895, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Seven-hundred milligrams (1.86 mmols) of (E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride, 478 mg of WSCI, 375 mg of HOBt.H2O and 486 mg of Boc-Gly were dissolved in 100 ml of N,N-dimethylformamide, and 0.35 ml of triethylamine were added thereto. The mixture was reacted at 50° C. for 3.5 hours. Seven-hundred milliliters of water were added thereto, and the resulting mixture was extracted with ethyl acetate. Subsequently, the ethyl acetate layer was washed three times with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, ether), and then dissolved in a small amount of dichloromethane. Diethyl ether was added thereto for crystallization to obtain 1.71 mmols of the final product in a yield of 92%.

Workup

  1. customThe mixture was reacted at 50° C. for 3.5 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washSubsequently, the ethyl acetate layer was washed three times with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified
  7. dissolutiondissolved in a small amount of dichloromethane
  8. additionDiethyl ether was added
  9. customfor crystallization

Sources & evidence

ORD record
ord-e6007c51b44d4833ab3b9511bdb036c1
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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