Triethylamine → HCID 22879062, compound

HRID 2293449Notes

Reaction equation

HRID 2293449 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:25])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:33]12([C:43](Cl)=[O:44])[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:25])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH:24][C:43]([C:33]23[CH2:42][CH:37]4[CH2:36][CH:35]([CH2:41][CH:39]([CH2:38]4)[CH2:40]2)[CH2:34]3)=[O:44])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 22873003HCID 22873003, compound

Product 1

HCID 22879062HCID 22879062, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

In a round bottom flask were added 1-[2-(S)-amino-4-methylpentyl]-L-proline 4-phenylbutylamide (20 mg), triethylamine (20 uL) and anhydrous dichloromethane (1 mL). 1-Adamantylcarbonyl chloride (17 mg) was added, and the reaction was stirred at 22° C. for 12 hours. The reaction mixture was washed with said aq NaHCO3, said aq NaCl, dried (MgSO4) and evaporated under reduced pressure. The crude reaction was chromatographed with acidic silica to provide 12 mg (42%) of the title compound. The 1H NMR and Mass spectrum analysis of this compound was consistent with the structure.

Workup

  1. washThe reaction mixture was washed
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe crude reaction
  5. customwas chromatographed with acidic silica

Sources & evidence

ORD record
ord-87bd0affff76434d8d74e9553ea37359
Source dataset
uspto-grants-1997_11
Patent number
US05686469

Reaction notes

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