1-Hydroxybenzotriazole → HCID 18654140, compound

HRID 1741663Notes

Reaction equation

HRID 1741663 reaction equation
C([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)(OC(C)(C)C)=O.ON1C2C=CC=CC=2N=N1.[ClH:33].CN(C)CCCN=C=NCC.[F:45][C:46]([F:60])([F:59])[C:47]1[CH:48]=[C:49]([CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1)[CH2:50][NH2:51]>CN(C)C=O.ClCCl.Cl>[ClH:33].[F:45][C:46]([F:59])([F:60])[C:47]1[CH:48]=[C:49]([CH:52]=[C:53]([C:55]([F:58])([F:56])[F:57])[CH:54]=1)[CH2:50][NH:51][C:20](=[O:22])[C@H: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)[NH2:8]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18654140HCID 18654140, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-Boc-L-tryptophan (5 g) and 1-hydroxybenzotriazole (2.48 g) in dimethyl formamide (85 ml) was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (3.15 g) at 0° C. After 30 minutes 3,5-bistrifluoromethylbenzylamine (4.43 g) was added and stirring continued for 16 hours at 25° C. The reaction mixture was diluted with dichloromethane and washed with sodium bicarbonate solution, water and dried (Na2SO4). The solvents were evaporated in vacuo to give a white solid which was dissolved in methanolic hydrogen chloride and allowed to stand for 16 hours. Concentration under reduced pressure afforded the title compound as a solid.

Workup

  1. washwashed with sodium bicarbonate solution, water
  2. dry with materialdried (Na2SO4)
  3. customThe solvents were evaporated in vacuo
  4. customto give a white solid which
  5. waitto stand for 16 hours
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7b662ef0727a4c3fbc9dca141b8b3f14
Source dataset
uspto-grants-1994_08
Patent number
US05334606

Reaction notes

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