Hydrochloric Acid → HCID 22877909, compound

HRID 1488857Notes

Reaction equation

HRID 1488857 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:42]([NH2:44])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(OC(C)(C)C)=O.[ClH:45].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:45].[NH2:33][C@H:34]([C:42]([NH2:44])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22877899HCID 22877899, compound

Product 1

HCID 22877909HCID 22877909, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Boc-L-phenylalanineamide (1,082 mg, 1.11 mmols) was dissolved in 10 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 chloroform, methanol and ethyl acetate at a ratio of 4:1:4 to produce 450 mg (0.859 mmols) of the final compound in a yield of 77%.

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 chloroform, methanol and ethyl acetate at a ratio of 4:1:4

Sources & evidence

ORD record
ord-e9908f572c704807b770514901913100
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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