Benzoic Acid → [(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoate

HRID 1796130Notes

Reaction equation

HRID 1796130 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([CH:11]([OH:16])[C:12](=[NH:15])[NH:13][OH:14])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([CH:11]([OH:16])[C:12](=[NH:15])[NH:13][O:14][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178456097HCID 178456097, compound

Product 1

HCID 178458006[(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoateYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {1-[hydroxy-(N-hydroxycarbamimidoyl)-methyl]-propyl}-carbamic acid tert-butyl ester (2) (2.5 g, 10 mmol) in dichloromethane (125 ml) was treated with benzoic acid (1.36 g, 11 mmol), EDCI (2.14 g, 11 mmol), HOBT (1.37 g, 10 mmol) and triethylamine (1.35 ml, 11 mmol) and stirred at room temperature overnight. Reaction mixture was washed with saturated sodium bicarbonate solution and then water and dried over Na2SO4. Solvent evaporated under reduced pressure, crude purified by mplc eluting with 1% triethylamine in 2:3 v/v ethyl acetate and heptane mixture to give yellow solid (850 mg); MS: MH+ 352.

Workup

  1. customReaction mixture
  2. washwas washed with saturated sodium bicarbonate solution
  3. dry with materialwater and dried over Na2SO4
  4. customSolvent evaporated under reduced pressure, crude
  5. custompurified
  6. washby mplc eluting with 1% triethylamine in 2:3 v/v ethyl acetate and heptane mixture

Sources & evidence

ORD record
ord-389dd286dcda4037910c7a7c493e3a33
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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