Hydrochloric Acid → HCID 178474437, compound

HRID 1246493Notes

Reaction equation

HRID 1246493 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:36]([N:38]2[CH2:43][CH2:42][CH:41]([C:44]([O:46]CC)=[O:45])[CH2:40][CH2:39]2)=[O:37])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]/[C:19](/[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([C:36]([N:38]2[CH2:43][CH2:42][CH:41]([C:44]([OH:46])=[O:45])[CH2:40][CH2:39]2)=[O:37])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]/[C:19](/[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178469244HCID 178469244, compound

Product 1

HCID 178474437HCID 178474437, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)phenyl]ethyl}-1,3-thiazol-5-yl)carbonyl]-4-piperidinecarboxylate (277.9 mg), 1N-NaOH (1.01 ml) and 1,4-dioxane (3 ml) were combined at 0° C., and the reaction mixture was stirred at r.t. for 3 hours. The mixture was neutrallized with 1N-HCl, and the organic solvent was evaporated in vacuo. The residual aqueous solution was extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo to give 1-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)phenyl]ethyl}-1,3-thiazol-5-yl)carbonyl]-4-piperidinecarboxylic acid (262.4 mg) as a pale yellow amorphous substance.

Workup

  1. customwere combined at 0° C.
  2. customthe organic solvent was evaporated in vacuo
  3. extractionThe residual aqueous solution was extracted with AcOEt
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f99c683374734bada665bf3de8dee45d
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

Loading…