Dibenzylamine → HCID 178454182, compound

HRID 1907131Notes

Reaction equation

HRID 1907131 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[NH:20]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CN([P+](Cl)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([N:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

7

Reactant 4

HCID 7656DibenzylamineHCID 81531DiisopropylethylamineHCID 16211753Chlorotri(1-pyrrolidinyl)phosphonium hexafluorophosphateHCID 178454187HCID 178454187, compound

Product 1

HCID 178454182HCID 178454182, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Boc-Arg-OH(1 eq), NH(CH2Ph)2 (1.1 eq) and PyCloP (1 eq) in dry DCM (filtered through alumina) (2 ml) and DMF (1 ml). The solution was cooled on ice and DIPEA (2 eq) was added under stirring. The solution was stirred for 1 h at room temperature. The reaction mixture was evaporated, and redissolved in ethyl acetate and washed with citric acid, sodium bicarbonate and brine. The solvent was removed under vacuum and the Boc protecting group of the resulting peptide was deprotected in the dark using 95% TFA.

Workup

  1. additionwas added
  2. stirringThe solution was stirred for 1 h at room temperature
  3. customThe reaction mixture was evaporated
  4. dissolutionredissolved in ethyl acetate
  5. washwashed with citric acid, sodium bicarbonate and brine
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4eb56d03af454cff85c6a47a66e96a2b
Source dataset
uspto-grants-2013_12
Patent number
US08598114B2

Reaction notes

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