Hydrochloric Acid → HCID 86595604, compound

HRID 2117914Notes

Reaction equation

HRID 2117914 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[N:18]=[C:19]([NH:33][C:34](=[O:38])[O:35][CH2:36][CH3:37])[S:20][C:21]=2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[N:18]=[C:19]([NH:33][C:34](=[O:38])[O:35][CH2:36][CH3:37])[S:20][C:21]=2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86595603HCID 86595603, compound

Product 1

HCID 86595604HCID 86595604, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl {4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}carbamate (140 mg) and 4N HCl in 1,4-dioxane solution (3 ml) were combined under N2 atmosphere. The reaction mixture was stirred at r.t. for 2 hours. The solvent was removed in vacuo. The residue was dissolved in water and AcOEt. The mixture was made basic (pH=8) by 1N—NaOH. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo to give ethyl {4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}carbamate (125.6 mg) as an off-white amorphous substance.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-508d94b53f5042ecb2999ee3f1fb4645
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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