Hydrochloric Acid → HCID 67828178, compound

HRID 1199100Notes

Reaction equation

HRID 1199100 reaction equation
[NH2:1][C:2]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.C(N1CCCCC1)C.[N+](C1C=CC([O:30][C:31](=O)[CH2:32][NH:33][C:34](=[O:48])[C@H:35]([CH3:47])[NH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=CC=1)([O-])=O>CN(C)C=O>[CH2:40]([O:39][C:37]([NH:36][C@H:35]([C:34]([NH:33][CH2:32][C:31]([CH:3]1[CH2:4][CH2:5][CH2:6][C:2]1([NH2:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:30])=[O:48])[CH3:47])=[O:38])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13007N-EthylpiperidineHCID 222862Ethyl 1-aminocyclopentane-1-carboxylateHCID 53738911HCID 53738911, compound

Product 1

HCID 67828178HCID 67828178, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide (25 ml) solution of ethyl 1-amino-1-cyclopentanecarboxylate liberated from its hydrochloride (1.0 g, 5 mmoles) with N-ethylpiperidine (0.7 ml) there was portionwise added benzyloxycarbonylalanyl-glycine p-nitrophenyl ester (2.1 g, 5 mmoles). After 3 hours of stirring and 12 hours of standing at room temperature the solution was evaporated, the residue was taken into ethyl acetate and extracted successively with 1% ammonia and water, dried over anhydrous sodium sulfate and evaporated. The residue was crystallized from ethyl acetate-petroleum ether to give 1.4 g (67%) of the title product, m.p. 119° to 121° C. An analytical sample was crystallized similarly, m.p. 137° to 139° L C. [α]D20 -3.4°.

Workup

  1. customof standing at room temperature
  2. customwas evaporated
  3. extractionextracted successively with 1% ammonia and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-cac77c09f4fb407290c16be87618e2e0
Source dataset
uspto-grants-1990_02
Patent number
US04898930

Reaction notes

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