1-Hydroxybenzotriazole → Diisopropylethylamine

HRID 1050723Notes

Reaction equation

HRID 1050723 reaction equation
[NH2:1][C@H:2]([C:8](O)=O)[CH2:3]CC(=O)O.[CH3:11][C:12]1C=CC(P(C2C=CC(C)=CC=2)CCP(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=C[CH:13]=1.[CH:43]1C=CC2N(O)N=NC=2[CH:48]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:43][CH2:48][N:1]([CH:2]([CH3:3])[CH3:8])[CH:12]([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 2724699PyBOPHCID 131729229HCID 131729229, compound

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The peptide on resin was suspended in DMF (5-7 mL/100 mg resin). In a separate vial, 1.5-2 eq of Glu-DTPE acid was activated by addition of HOBt, and PyBOP in DMF (10% of the volume of peptide mixture) for 5-10 min at pH≈8 obtained by addition of DIEA (measured with wet pH paper). Activated DTPE acid mixture was added to the solution of peptide and the pH was adjusted to ˜8 with DIEA. The mixture was shaken at RT for 4-18 hours.

Sources & evidence

ORD record
ord-f1a7783dded94f01a486dcdb07f9c286
Source dataset
uspto-grants-2016_07
Patent number
US09386938B2

Reaction notes

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