1-Hydroxybenzotriazole → HCID 67140010, compound

HRID 1592037Notes

Reaction equation

HRID 1592037 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]=1)[C:8](O)=[O:9])=[O:5].C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:22]([O:21][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[N+:18]([O-:20])=[O:19])[CH2:11][CH:7]1[NH:6][C:4](=[O:5])[C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]=2[NH:1][C:8]1=[O:9])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67138197HCID 67138197, compound

Product 1

HCID 67140010HCID 67140010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title I compound, 2-(2-amino-benzoylamino)-3-(3-benzyloxy-4-nitro-phenyl)-propionic acid (317 mg, 0.728 mmol) in CH2Cl2 (10 mL) is added HOBt (111.5 mg, 0.728 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC.HCl, 140 mg, 0,72 mmol) and the mixture is stirred at RT for 4 h and evaporated. The residue is partitioned between EtOAc and water and the organic solution is washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, decolorized and evaporated to a small volume. The precipitated product is collected by filtration and dried to give 3-(3-benzyloxy-4-nitro-benzyl)-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione: mp=243-245° C.

Workup

  1. customevaporated
  2. customThe residue is partitioned between EtOAc and water
  3. washthe organic solution is washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated to a small volume
  6. filtrationThe precipitated product is collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-402b631582174aa7a5500ec819f0fd65
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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