1-Hydroxybenzotriazole → HCID 481576, compound

HRID 1596326Notes

Reaction equation

HRID 1596326 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:37]([NH:41][C:42]([C@@H:44]1[C:48]([CH3:50])([CH3:49])[S:47][CH2:46][N:45]1[C:51](=[O:69])[C@@H:52]([OH:68])[C@@H:53]([NH:61][C:62](=[O:67])[C@@H:63]([NH2:66])[CH2:64][CH3:65])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C.C(OCC)(=O)C>[C:37]([NH:41][C:42]([C@@H:44]1[C:48]([CH3:50])([CH3:49])[S:47][CH2:46][N:45]1[C:51](=[O:69])[C@@H:52]([OH:68])[C@@H:53]([NH:61][C:62](=[O:67])[C@@H:63]([NH:66][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([N:2]([CH3:1])[CH3:14])[CH:4]=1)[CH2:64][CH3:65])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:43])([CH3:38])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21701158HCID 21701158, compoundHCID 70249319HCID 70249319, compound

Product 1

HCID 481576HCID 481576, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-dimethylaminophenoxyacetic acid (51 mg), HOBt (35mg), and EDC.HCl (53 mg) were added to a solution of H-Abu-Apns-Dmt-NHtBu (120 mg) obtained in the step 1 in DMF and the mixture was stirred overnight. After the addition of ethyl acetate, the reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was purified using silica gel column chromatography to obtain the title compound (120 mg).

Workup

  1. washthe reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified

Sources & evidence

ORD record
ord-3f2effad19ba4e6894b18f6732bedf7d
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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