Hydrochloric Acid → HCID 9936605, compound

HRID 381524Notes

Reaction equation

HRID 381524 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].CO[C:8](=[O:42])[CH2:9][CH2:10][C:11]1[S:15][C:14]([CH:16]([NH:21][C:22](=[O:41])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[CH:26][CH:25]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])=[N:13][CH:12]=1.Cl>CO>[OH:3][NH:2][C:8](=[O:42])[CH2:9][CH2:10][C:11]1[S:15][C:14]([CH:16]([NH:21][C:22](=[O:41])[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[CH:28][CH:29]=2)[CH2:17][CH:18]([CH3:19])[CH3:20])=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 54409632HCID 54409632, compound

Product 1

HCID 9936605HCID 9936605, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

Hydroxylamine hydrochloride (6.96 g) was suspended in methanol ( 35 mL) and heated to 90° C. This solution was added to potassium hydroxide (8.34 g) dissolved in methanol (21 mL) After 15 minutes of stirring, the solution was filtered and 3-[2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-thiazol-5-yl]propionic acid methyl ester (0.80 g, 1.53 mmol) was added. The reaction was stirred at room temperature for 15 minutes, 1N HCl (50 mL) was added, and the methanol was removed in vacuo. The residue was partitioned between ethyl acetate and hydrochloric acid (1N). The organic portion was dried over sodium sulfate and the solvent removed in vacuo. The title compound (0.175 g, 17%) was isolated by crystallization from a mixture of ethyl acetate and methanol. MS [M+1] 524.1.

Workup

  1. filtrationthe solution was filtered
  2. stirringThe reaction was stirred at room temperature for 15 minutes
  3. customthe methanol was removed in vacuo
  4. customThe residue was partitioned between ethyl acetate and hydrochloric acid (1N)
  5. dry with materialThe organic portion was dried over sodium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e6fc3eccfefc43398e6d32218f9be3a4
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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