1-Hydroxybenzotriazole → HCID 86627963, compound

HRID 251739Notes

Reaction equation

HRID 251739 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.O[NH:64][C:65]([C:67]1[CH:76]=[CH:75][C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[CH:68]=1)=[NH:66]>CN(C=O)C>[CH:68]1[C:69]2[C:74](=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH:75]=[CH:76][C:67]=1[C:65]1[N:64]=[C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[O:12][N:66]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11197378HCID 11197378, compoundHCID 178513226HCID 178513226, compound

Product 1

HCID 86627963HCID 86627963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid (1 eq), TBTU (1.2 eq), HOBt (0.2 eq) and DIPEA (5 eq) in DMF was stirred at RT for 5 min; then added N-hydroxynaphthalene-2-carboximidamide was added and the mixture was stirred at RT for 20 min, after which time the mixture was warmed to 110° C. for 2 h. The solvent was removed under reduced pressure and the resulting crude used as such in the next step. MS (ES) C26H33N3O4 requires: 451, found: 452 (M+H+).

Workup

  1. stirringthe mixture was stirred at RT for 20 min
  2. temperatureafter which time the mixture was warmed to 110° C. for 2 h
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9b7dc499915b40b989ebc269a7f0848d
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

Loading…