Triethylamine → HCID 10717394, compound

HRID 865502Notes

Reaction equation

HRID 865502 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[Cl:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH2:40]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:20]([NH:40][CH2:39][C:38]1[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=1[Cl:36])=[O:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 666482-ChlorobenzylamineHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 10717394HCID 10717394, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(t-butoxycarbonyl)tryptophan (21.28 g, 70 mmol) in 140 ml of acetone was added triethylamine (9.76 ml, 7.08 g, 70 mmol) in a portionwise manner. The resulting mixture was stirred for about thirty-five minutes at room temperature and then stirred at 45° C. for 30 minutes under nitrogen. To the resulting mixture ethyl chloroformate (7.35 ml, 8.36 g, 77 mmol) was added with continued cooling and the reaction mixture was stirred for about one hour. Next, 2-chlorobenzylamine (9.30 ml, 10.9 g, 77 mmol) was added and the reaction mixture was then stirred until a white precipitate formed. The ice bath was removed and additional acetone was added. The reaction mixture was then stirred overnight.

Workup

  1. stirringstirred at 45° C. for 30 minutes under nitrogen
  2. temperaturewith continued cooling
  3. stirringthe reaction mixture was stirred for about one hour
  4. stirringthe reaction mixture was then stirred until a white precipitate
  5. customformed
  6. customThe ice bath was removed
  7. additionadditional acetone was added
  8. stirringThe reaction mixture was then stirred overnight

Sources & evidence

ORD record
ord-3fbb006110764961a28f242b959e6be4
Source dataset
uspto-grants-1996_10
Patent number
US05565568

Reaction notes

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