Hydrochloric Acid → HCID 59853929, compound

HRID 2061258Notes

Reaction equation

HRID 2061258 reaction equation
Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[C:20]([NH:26][C@H:27]([C:30]([OH:32])=O)[CH2:28][OH:29])(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].[CH:33]1[C:43]2[CH:42]=[CH:41][C:40]3[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=3[C:38](=[C:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)[C:37]=2[CH:36]=[CH:35][CH:34]=1.Cl>ClCCl>[CH:33]1[C:43]2[CH:42]=[CH:41][C:40]3[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=3[C:38](=[C:48]3[CH2:49][CH2:50][N:51]([C:30](=[O:32])[C@@H:27]([NH:26][C:20](=[O:25])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:28][OH:29])[CH2:52][CH2:53]3)[C:37]=2[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30048360HCID 30048360, compound

Product 1

HCID 59853929HCID 59853929, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

880 mg (4.59 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 0.63 ml (4.52 mmol) of triethylamine and 860 mg (4.55 mmol) of pivaloyl-L-serine were added to 1.231 g (4.50 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)piperidine in 20 ml of dichloromethane in ice bath, and they were stirred at room temperature overnight. 1 N hydrochloric acid was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:2) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:2)

Sources & evidence

ORD record
ord-0acd766e7bf84300a848ac91cfdf3ca2
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

Loading…