Hydrochloric Acid → HCID 67827731, compound

HRID 1199095Notes

Reaction equation

HRID 1199095 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:22]([OH:24])=O)[CH3:21])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:48][C:49]1([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:53][CH2:52][CH2:51][CH2:50]1.Cl.C(N1CCCCC1)C>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:22]([CH:50]1[CH2:51][CH2:52][CH2:53][C:49]1([NH2:48])[C:54]([O:56][CH2:57][CH3:58])=[O:55])=[O:24])[CH3:21])=[O:18])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 13007N-EthylpiperidineHCID 80170N-HydroxysuccinimideHCID 222862Ethyl 1-aminocyclopentane-1-carboxylateHCID 69924752817-13-2

Product 1

HCID 67827731HCID 67827731, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a solution of benzyloxycarbonylleucyl-alanine (6.72 g, 20 mmoles) in dimethylformamide (70 ml) was added N-hydroxysuccinimide (2.3 g. 20 mmoles) and on cooling to -5° C. N,N'-dicyclohexyl-carbodiimide (4.4 g) was admixed. After 1 hour of stirring and cooling (-5° C.) there was added a dimethylformamide (40 ml) solution of ethyl 1-amino-1-cyclopentanecarboxylate liberated from its hydrochloride (3.86 g, 20 mmoles) with N-ethylpiperidine (2.8 ml) and the reaction mixture was stirred for further 2 hours at room temperature. After subsequent 12 hours of standing, the N,N'-dicyclohexylurea precipitate was filtered off, washed with dimethylformamide and the filtrate was evaporated. The residue was dissolved in an ethyl acetate-water mixture and the organic phase was shaken 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 (25 ml) and petroleum ether (200 ml) to give 7.6 g (80%) of the title compound, m.p. 102° to 104° C., after similar recrystallization 104° to 106° C. [α]D20 -35.9° (c 0.2, methanol).

Workup

  1. temperaturecooling (-5° C.) there
  2. stirringthe reaction mixture was stirred for further 2 hours at room temperature
  3. waitAfter subsequent 12 hours of standing
  4. filtrationthe N,N'-dicyclohexylurea precipitate was filtered off
  5. washwashed with dimethylformamide
  6. customthe filtrate was evaporated
  7. dissolutionThe residue was dissolved in an ethyl acetate-water mixture
  8. stirringthe organic phase was shaken successively with 1M hydrochloric acid, water, 5% sodium hydrogencarbonate and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. customThe residue was crystallized from ethyl acetate (25 ml) and petroleum ether (200 ml)

Sources & evidence

ORD record
ord-a9cd0c52429f404388c91c434c536fc6
Source dataset
uspto-grants-1990_02
Patent number
US04898930

Reaction notes

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