Hydrochloric Acid → HCID 178462107, compound

HRID 1746237Notes

Reaction equation

HRID 1746237 reaction equation
CO[C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Cl:16])[CH:9]=2)=[O:4].[NH2:18][C@H:19]([C:21]([OH:23])=[O:22])[CH3:20].C[O-].[Na+].Cl>COCCO>[Cl:16][C:10]1[CH:9]=[C:8]2[C:13]([C:14]([OH:15])=[C:5]([C:3]([NH:18][C@@H:19]([CH3:20])[C:21]([OH:23])=[O:22])=[O:4])[C:6](=[O:17])[S:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 178498941HCID 178498941, compound

Product 1

HCID 178462107HCID 178462107, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 7-chloro-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Compound 60 (f)) (125 mg, 0.46 mmol), L-alanine (494 mg, 5.55 mmol) and NaOMe (249 mg, 4.62 mmol) in 2-methoxyethanol (5 mL) was heated in a 115° C. sand bath for 24 h. 1 N HCl aq. solution was added to precipitate the product. The solid was collected and rinsed with water. It was dried in vacuo and then triturated with MeOH to provide the title compound (102 mg). MS ESI(−) m/e: 327.96, 325.97 (M−1).

Workup

  1. customto precipitate the product
  2. customThe solid was collected
  3. washrinsed with water
  4. customIt was dried in vacuo
  5. customtriturated with MeOH

Sources & evidence

ORD record
ord-7671e7df02644428923d704960e0c480
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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