Hydrochloric Acid → HCID 66712928, compound

HRID 523688Notes

Reaction equation

HRID 523688 reaction equation
C[O-].[Na+].CO[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[SH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7].[NH2:26][C@H:27]([C:29]([OH:31])=[O:30])[CH3:28].Cl>CO.O>[SH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][C@@H:27]([CH3:28])[C:29]([OH:31])=[O:30])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 66712886HCID 66712886, compound

Product 1

HCID 66712928HCID 66712928, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6.0 ml of 0.5 M sodium methoxide in methanol was added 100 mg of 4-Mercapto-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester and 286 mg of L-alanine. The mixture was heated to 150° C. for 15 minutes using a CEM Discover microwave reactor. The resultant solution was acidified to pH 3 with 1N HCl, diluted with 10 ml water, and extracted with 20 ml of ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to 114 mg of product; MS (−): m/z 369.07 (M−1).

Workup

  1. extractionextracted with 20 ml of ethyl acetate
  2. washThe organic fraction was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to 114 mg of product

Sources & evidence

ORD record
ord-d7772ae101d04b64af103ce5dda3df1e
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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