Hydrochloric Acid → 2-Amino-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamide

HRID 45398Notes

Reaction equation

HRID 45398 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16]C(OC(C)(C)C)=O)=[N:13][C:12]=1[CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86642524HCID 86642524, compound

Product 1

HCID 866425232-Amino-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamideYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 2-(tert-butoxycarbonylamino)-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamide (0.18 mmol) from the previous step in methanol (5 mL) was treated with hydrochloric acid solution (3 mL, 4 M solution in dioxanes) and the reaxtion mixture was stirred at ambient temperature until the reaction was completed. The mixture was then concentrated and purified by preparative HPLC (acetone/water gradient) to afford 2-amino-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamide (0.030 g).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by preparative HPLC (acetone/water gradient)

Sources & evidence

ORD record
ord-fe00990f720e4daa9b977897cfba0687
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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