1-Hydroxybenzotriazole → HCID 59773381, compound

HRID 2114296Notes

Reaction equation

HRID 2114296 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]([OH:39])=O)=[O:34])([CH3:31])([CH3:30])[CH3:29].CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[C:28]([O:32][C:33](=[O:34])[NH:35][CH2:36][C:37](=[O:39])[N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)([CH3:29])([CH3:30])[CH3:31]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 1230984-(Methylamino)pyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59773381HCID 59773381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.1 eq. of 4-(methylamino)pyridine (180, Aldrich, 19,551-0) in anhydrous DMF was stirred under an atmosphere of argon as 1.1 eq. of HOBT and 2.0 eq of DIPEA were added followed by 1.0 eq of N-(tert-butoxycarbonyl)glycine (Bachem, A-1730). The mixture was stirred for 1 hr, cooled in an ice-bath and 1.1 eq. of EDC.HCl was added. The reaction was stirred and allowed to reach rt overnight. Water was added to the reaction mixture and the solvents were evaporated under high vacuum. The residue was dissolved in ethyl acetate, washed with 0.15 M citric acid, sat. aq. NaHCO3, brine and dried over anhydrous Na2SO4. To afford 181.

Workup

  1. additionwere added
  2. temperaturecooled in an ice-bath
  3. stirringThe reaction was stirred
  4. waitto reach rt overnight
  5. customthe solvents were evaporated under high vacuum
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with 0.15 M citric acid, sat. aq. NaHCO3, brine
  8. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-0deb10ebb8214b7b997942030c1c1ec6
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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