Hydrochloric Acid → HCID 15166649, compound

HRID 1199098Notes

Reaction equation

HRID 1199098 reaction equation
[C:1]([NH:4][C@H:5]([C:17]([OH:19])=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C(N1CCCCC1)C.ClC(OCC)=O.[CH3:34][O:35][C:36](=[O:40])[C@H:37]([CH3:39])[NH2:38].Cl>O1CCCC1>[CH3:34][O:35][C:36](=[O:40])[C@H:37]([CH3:39])[NH:38][C:17](=[O:19])[C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14](=[O:16])[CH3:15])=[CH:11][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 13007N-Ethylpiperidine2×HCID 82335L-Alanine methyl esterHCID 87072O-Acetyl-N-(1-hydroxyethylidene)tyrosine

Product 1

HCID 15166649HCID 15166649, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,O-diacetyltyrosine (13.3 g, 50 mmoles) and N-ethylpiperidine (7 ml) in tetrahydrofurane (100 ml) precooled to -15° C. was added ethyl chloroformate (5 ml). After 15 minutes of stirring and cooling (-15° C.) alanine methyl ester liberated from its hydrochloride (7.0 g, 50 mmoles) with N-ethylpiperidine (7 ml) was admixed. After 2 hours of stirring at 0° C. and 12 hours of standing at room temperature, the solution was evaporated, the residue was taken into ethyl acetate and the organic phase was successively washed with 1M hydrochloric acid, water, 5% sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate and evaporated. Crystallization from 2-propanol-petroleum ether yielded 10.6 g (60%) of the title product. An analytical sample was recrystallized similarly, m.p. 173° to 176° C. [α]D20 -7.5°.

Workup

  1. customprecooled to -15° C.
  2. stirringAfter 2 hours of stirring at 0° C. and 12 hours
  3. customof standing at room temperature
  4. customthe solution was evaporated
  5. washthe organic phase was successively washed with 1M hydrochloric acid, water, 5% sodium hydrogencarbonate and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customCrystallization from 2-propanol-petroleum ether

Sources & evidence

ORD record
ord-c8af05b093024c689dc63dbc07404011
Source dataset
uspto-grants-1990_02
Patent number
US04898930

Reaction notes

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