Triethylamine → HCID 14459514, compound

HRID 611964Notes

Reaction equation

HRID 611964 reaction equation
C(N(CC)CC)C.Br.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:18]([C:20]2[C:21]3[C:26]([N:27]=[C:28]4[C:33]=2[CH:32]=[CH:31][CH:30]=[CH:29]4)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])=[CH:13][CH:12]=1.ClC(OCC)=O.O[N:55]1[C:59](=[O:60])[CH2:58][CH2:57][C:56]1=[O:61]>O1CCCC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([S:34]([C:37]2[CH:38]=[CH:39][C:40]([CH2:43][CH2:44][C:45]([O:47][N:55]3[C:59](=[O:60])[CH2:58][CH2:57][C:56]3=[O:61])=[O:46])=[CH:41][CH:42]=2)(=[O:36])=[O:35])[C:18]([C:20]2[C:33]3[C:28]([N:27]=[C:26]4[C:21]=2[CH:22]=[CH:23][CH:24]=[CH:25]4)=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:19])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 80170N-HydroxysuccinimideHCID 14459513HCID 14459513, compound

Product 1

HCID 14459514HCID 14459514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1.41 ml of triethylamine are added to 3.1 g of (4) in 50 ml of tetrahydrofuran, the mixture is cooled to -20° C., and 0.474 ml of ethyl chloroformate is added. After stirring for 20 min, 575 mg of N-hydroxysuccinimide are added, and the mixture is stirred at -20° C. for 3 hours and left to reach room temperature overnight while stirring. The precipitate is filtered off with suction, the filtrate is concentrated, the residue is taken up in dichloromethane or ethyl acetate, and the resulting solution is washed with water, NaHCO3 solution and water and dried over MgSO4. The organic phase is concentrated, and the residue is recrystallized from toluene.

Workup

  1. stirringthe mixture is stirred at -20° C. for 3 hours
  2. waitleft
  3. waitto reach room temperature overnight
  4. stirringwhile stirring
  5. filtrationThe precipitate is filtered off with suction
  6. concentrationthe filtrate is concentrated
  7. washethyl acetate, and the resulting solution is washed with water, NaHCO3 solution and water
  8. dry with materialdried over MgSO4
  9. concentrationThe organic phase is concentrated
  10. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-0b767c4df6544dadbe2487fd1dd74f10
Source dataset
uspto-grants-1999_12
Patent number
US06002007

Reaction notes

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