Hydrochloric Acid → HCID 22877908, compound

HRID 1488856Notes

Reaction equation

HRID 1488856 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([NH:33][C@H:34]([C:39]([NH2:41])=[O:40])[CH2:35][CH2:36][CH2:37][NH2:38])(OC(C)(C)C)=O.[ClH:42].O1CCOCC1.C(OCC)C>ClCCl>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[ClH:42].[NH2:33][C@H:34]([C:39]([NH2:41])=[O:40])[CH2:35][CH2:36][CH2:37][NH2:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22877898HCID 22877898, compound

Product 1

HCID 22877908HCID 22877908, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(3Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Boc-L-ornithineamide (730 mg, 1.11 mmols) was dissolved in 5 ml of dichloromethane, and 5 ml of a solution of 4-M hydrochloric acid and dioxane were added thereto. The mixture was reacted at room temperature for 1 hour. One-hundred milliliters of diethyl ether were added thereto, and the resulting mixture was filtered. The thus-obtained powder was recrystallized from a mixture of methanol and ethyl acetate at a ratio by volume of 1:1 to produce 286 mg (0.542 mmols) of the final compound in a yield of 48%.

Workup

  1. customThe mixture was reacted at room temperature for 1 hour
  2. filtrationthe resulting mixture was filtered
  3. customThe thus-obtained powder was recrystallized from a mixture of methanol and ethyl acetate at a ratio by volume of 1:1

Sources & evidence

ORD record
ord-153f55c023564eab98bea61ce9d8be52
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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