Hydrochloric Acid → HCID 15166647, compound

HRID 1199096Notes

Reaction equation

HRID 1199096 reaction equation
ClC1C(O[C:9](=[O:29])[C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15](=[O:28])[CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=C(Cl)C(Cl)=C(Cl)C=1Cl.[CH3:34][O:35][C:36](=[O:40])[C@H:37]([CH3:39])[NH2:38].Cl.C(N1CCCCC1)C>CN(C)C=O>[CH3:34][O:35][C:36](=[O:40])[C@H:37]([CH3:39])[NH:38][C:9](=[O:29])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:28])[CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13007N-EthylpiperidineHCID 82335L-Alanine methyl esterHCID 54027550HCID 54027550, compound

Product 1

HCID 15166647HCID 15166647, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyloxycarbonylglycyl-proline pentachlorophenyl ester (5.55 g, 10 mmoles) in dimethylformamide (30 ml) was added alanine methyl ester liberated from its hydrochloride (1.4 g, 10 mmoles) with N-ethylpiperidine (1.4 ml). After 5 hours of a stirring and 12 hours of standing at room temperature the solution was evaporated, the residue was taken into ethyl acetate and the organic phase was washed successively with 1M hydrochloric acid, water, 5% sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate and evaporated. The residue was crystallized from ethyl acetate-petroleum ether to give 1.95 g (50%) of the title product, m.p. 103° to 106° C. An analytical sample was recrystallized similarly, m.p. 105° to 108° C. [α]D20 -100.1° (c 0.2, MeOH).

Workup

  1. customthe solution was evaporated
  2. washthe organic phase was washed successively with 1M hydrochloric acid, water, 5% sodium hydrogencarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-efdf225f870f4bce9c85f0a1f18f404f
Source dataset
uspto-grants-1990_02
Patent number
US04898930

Reaction notes

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