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

HRID 250316Notes

Reaction equation

HRID 250316 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-cecb93e191c04127897f950056f5a74c
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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