PyBOP → 1-Hydroxybenzotriazole

HRID 446173Notes

Reaction equation

HRID 446173 reaction equation
C1CN([P+]([O:17][N:18]2[N:26]=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C[NH-]>>[CH:22]1[CH:23]=[CH:24][C:19]2[N:18]([OH:17])[N:26]=[N:25][C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 2724699PyBOPHCID 21952893Methylamide

Product 1

HCID 757711-HydroxybenzotriazoleYield 93%

Procedure

Because 36 could be prepared very cleanly without any of the bis-acylated product using PS-CCD or PyBOP, ester 36 was converted to N-methyl amide 38 (Scheme 6). Ester 36 was cleanly obtained on a preparative scale from 35 using PS-CCD and HOBt in the absence of base. After purification of 36 only by filtration and aqueous extraction, heating at 90° C. in toluene under anhydrous conditions provided the desired amide product 38 in 93% yield over the two steps.

Workup

  1. customBecause 36 could be prepared very cleanly without any of the bis-acylated product

Sources & evidence

ORD record
ord-bae747544ba5411295e220473d8210db
Source dataset
uspto-grants-2013_07
Patent number
US08476451B2

Reaction notes

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