1-Hydroxybenzotriazole → HCID 178418300, compound

HRID 477573Notes

Reaction equation

HRID 477573 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:9](O)[N:8]=[N:7][C:5]=2[CH:6]=1.CN([P+]([O:21]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>>[OH:21][C:6]1[C:5]2[N:7]=[N:8][NH:9][C:4]=2[CH:3]=[CH:2][CH:1]=1

Participants

3

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 178418300HCID 178418300, compound

Procedure

Competition experiments demonstrate that under the reaction conditions followed the BOP Reagent functions to form the symmetrical acid anhydride within about one minute. During the remaining ten minutes of preactivation mixing a portion of the symmetrical anhydride is converted by HOBt liberated from the BOP Reagent to form an intermediate hydroxybenzotriazole active ester. This active ester intermediate then couples with the available reactive functionalities on the synthesis resin or the coupled amino acid in the peptide chain.

Sources & evidence

ORD record
ord-c567df1cdc1f4a46af9bace1939627a1
Source dataset
uspto-grants-1989_12
Patent number
US04888385

Reaction notes

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