1-Hydroxybenzotriazole → HCID 178501454, compound

HRID 519413Notes

Reaction equation

HRID 519413 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:23][C@H:24]([C:32]([O:34][CH3:35])=[O:33])[CH2:25][CH2:26][CH2:27][NH:28][C:29](=[NH:31])[NH2:30].Cl.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.ClCCl.C(OCC)(=O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([NH:23][C@H:24]([C:32]([O:34][CH3:35])=[O:33])[CH2:25][CH2:26][CH2:27][NH:28][C:29](=[NH:30])[NH2:31])=[O:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178418801HCID 178418801, compound

Product 1

HCID 178501454HCID 178501454, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Boc-L-Trp-OH (761 mg, 2.5 mmoles), H-L-Arg-OMe dihydrochloride (718 mg, 2.75 mmoles), HOBt (1378 mg, 9 mmoles) and DIPEA (2.05 ml, 12 mmoles) in DMF (5 ml) and dichloromethane (2 ml) cooled on ice was added HBTU (1138 mg, 3 mmoles) in small portions over 10 minutes. The mixture was stirred on ice for 1 hour, 40 ml ethyl acetate was added and the organic phase washed successively with 3×40 ml saturated NaHCO3, 2×30 ml 5% citric acid, 50 ml water and 2×30 ml brine. Evaporation afforded 1.1 g of a white solid.

Workup

  1. washthe organic phase washed successively with 3×40 ml saturated NaHCO3, 2×30 ml 5% citric acid, 50 ml water and 2×30 ml brine
  2. customEvaporation

Sources & evidence

ORD record
ord-b8aec0202cd647fead3ef8ed0a307028
Source dataset
uspto-grants-2015_08
Patent number
US09115169B2

Reaction notes

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