1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178474744, compound

HRID 1698882Notes

Reaction equation

HRID 1698882 reaction equation
[ClH:1].C(O[C:5](=[NH:8])[CH2:6][F:7])C.[C:9]([NH:12][CH:13]([CH2:17][C:18]#[C:19][CH2:20][NH2:21])[C:14]([OH:16])=[O:15])(=[O:11])[CH3:10].C1CCN2C(=NCCC2)CC1>C(O)C>[ClH:1].[C:9]([NH:12][CH:13]([CH2:17][C:18]#[C:19][CH2:20][NH:21][C:5](=[NH:8])[CH2:6][F:7])[C:14]([OH:16])=[O:15])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 122535083862-78-0HCID 14235670HCID 14235670, compound

Product 1

HCID 178474744HCID 178474744, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Ex-8h) 2.86 g of ethylfluoroacetimidate hydrochloride, 1 equivalent of 2-acetylamino-6-amino-4-hexynoic acid and 6.84 g of DBU are taken up in 200 mL absolute ethanol and stirred for 16 h at 20° C. under argon. Solvent is removed under vacuum and 100 mL water is added. This reaction mixture is filtered through acidic ion exchange column and the product is eluted with 10% pyridine/water. (±)-2-Acetylamino-6-(1-imino-2-fluoroethylamino)-hex-4-ynoic acid hydrochloride is obtained by removing the solvent under vacuum.

Workup

  1. customSolvent is removed under vacuum and 100 mL water
  2. additionis added
  3. filtrationThis reaction mixture is filtered through acidic ion exchange column
  4. washthe product is eluted with 10% pyridine/water

Sources & evidence

ORD record
ord-0aeb24a0428642a6a98ff5b1cc7ca74f
Source dataset
uspto-grants-2002_02
Patent number
US06344483B1

Reaction notes

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