Hydrochloric Acid → HCID 13750023, compound

HRID 1583728Notes

Reaction equation

HRID 1583728 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].Cl.C(N1CCCCC1)C>C(Cl)Cl>[CH3:19][O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH:23][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13007N-EthylpiperidineHCID 82335L-Alanine methyl esterHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 13750023HCID 13750023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

11.0 grams of N,N-dicyclohexylbodiimide was added to a solution of 12.45 grams of benzyloxycarbonyl proline and alanine methyl ester released from 7.0 grams of the corresponding hydrochloride using 7 ml of N-ethyl piperidine in 40 ml of methylene chloride cooled to -5 degrees C. The resultant reaction suspension was stirred for 1 hour at 0 degree C. N,N-dicyclohexylurea separated from the suspension and was filtered off after it was allowed to stand for 12 hours at 3 degrees C. Then, the filtrate was successively washed with 1M hydrochloric acid, water, 5% sodium hydrogen carbonate, with water, dried with anhydrous sodium sulfate and evaporated. A solid evaporation residue was crystallized from 100 ml of ethyl acetate and 500 ml of petroleum ether. 12.2 g of a product having a melting point of 45 to 49 degrees C. was obtained.

Workup

  1. customThe resultant reaction suspension
  2. customN,N-dicyclohexylurea separated from the suspension
  3. filtrationwas filtered off after it
  4. waitto stand for 12 hours at 3 degrees C
  5. washThen, the filtrate was successively washed with 1M hydrochloric acid, water, 5% sodium hydrogen carbonate, with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated
  8. customA solid evaporation residue
  9. customwas crystallized from 100 ml of ethyl acetate and 500 ml of petroleum ether
  10. customwas obtained

Sources & evidence

ORD record
ord-852c60a95b2a4e86a6da2cc8409e4101
Source dataset
uspto-grants-1985_11
Patent number
US04554100

Reaction notes

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