Triethylamine → (S)-2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester

HRID 1866264Notes

Reaction equation

HRID 1866264 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[N:3]=1.C(N(CC)CC)C.Cl.[CH3:24][O:25][C:26](=[O:30])[C@H:27]([CH3:29])[NH2:28]>C(Cl)Cl>[CH3:24][O:25][C:26](=[O:30])[C@@H:27]([NH:28][C:13]([C:4]1[N:3]=[C:2]([Cl:1])[C:11]2[C:6]([C:5]=1[OH:12])=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:15])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acid

Product 1

HCID 86595456(S)-2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid, 0.55 g, 1.5 ml of triethylamine, 0.55 g of DECI, and 0.56 g of (L)-Alanine methyl ester hydrochloride were stirred in 15 ml of methylene chloride at room temperature for 72 h. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was separated and successively washed with 1M aqueous HCl, satd. aqueous NaHCO3, and satd. aqueous NaCl. The organic layer was dried with sodium sulfate, filtered, and concentrated under vacuum to afford 0.133 g of off-white solid product: MS-(+)-ion, M+1=308.9 Daltons.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe organic layer was separated
  3. washsuccessively washed with 1M aqueous HCl
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a90c73f61acc424dbcd754c09b10260f
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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