Chlorotrimethylsilane → alpha-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-furylacetic acid

HRID 1075185

Reaction equation

HRID 1075185 reaction equation
[NH2:1][CH:2]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[C:3]([OH:5])=[O:4].C[Si](C)(C)Cl.[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24](Cl)=[O:25])[C:20](=[O:27])[C:19]1=[O:28])[CH3:17].Cl.C(N(CC)CC)C>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([NH:1][CH:2]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[C:3]([OH:5])=[O:4])=[O:25])[C:20](=[O:27])[C:19]1=[O:28])[CH3:17]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 11130Triethylamine hydrochlorideHCID 1088134-Ethyl-2,3-dioxopiperazinecarbonyl chlorideHCID 2983852-Amino-2-(furan-2-yl)acetic acid

Product 1

HCID 15573352alpha-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-furylacetic acidYield 85.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To an ice-cooled suspension of 2.55 g of DL-α-amino-2-furylacetic acid in 35 ml of methylene chloride was added 4.81 ml of trimethylchlorosilane. To the resulting mixture was added dropwise 5.04 ml of triethylamine over a period of 10 minutes at 5° to 10° C. The reaction was allowed to proceed at 15° to 20° C. for one hour. To the reaction mixture was added over a period of 15 minutes at 5° to 10° C. 7.01 g of a mixture of 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride and triethylamine hydrochloride, said mixture containing 58.02% of the former. The reaction was allowed to proceed at 10° to 15° C. for one hour. After addition of 20 ml of water, the reaction mixture was stirred at room temperature for one hour, then at 5° to 7° C. for 30 minutes. The precipitated crystals were collected by filtration, washed with 5 ml of methylene chloride and 5 ml of water in this order, and then dried to obtain 4.75 g of DL-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-furylacetic acid, m.p. 179°-181° C. (decomp.), yield 85.6%.

Workup

  1. additionTo the reaction mixture was added over a period of 15 minutes at 5° to 10° C
  2. additioncontaining 58.02% of the former
  3. waitto proceed at 10° to 15° C. for one hour
  4. waitat 5° to 7° C. for 30 minutes
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with 5 ml of methylene chloride and 5 ml of water in this order
  7. customdried

Sources & evidence

ORD record
ord-817204799dfb4e57a572672069df7a31
Source dataset
uspto-grants-1983_07
Patent number
US04395412

Linked notes

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