Trifluoroacetic acid → (R)-2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-3-hydroxy-propionic acid

HRID 1406069Notes

Reaction equation

HRID 1406069 reaction equation
C([O:5][C:6](=[O:29])[C@H:7]([NH:14][C:15]([C:17]1[N:18]=[C:19]([Cl:28])[C:20]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[CH2:8][O:9]C(C)(C)C)(C)(C)C.FC(F)(F)C(O)=O>>[Cl:28][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]([OH:27])=[C:17]([C:15]([NH:14][C@H:7]([CH2:8][OH:9])[C:6]([OH:29])=[O:5])=[O:16])[N:18]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86595447(R)-3-tert-Butoxy-2-[(1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester

Product 1

HCID 86595448(R)-2-[(1-Chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-3-hydroxy-propionic acidYield 144.8%

Procedure

A mixture of 27 mg (0.06 mmol) of (R)-3-tert-Butoxy-2-[(1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester and 2 ml of trifluoroacetic acid was stirred for 2 h at ambient temperature. Then the excess trifluoroacetic acid was evaporated in vacuo, the residue dissolved in 2 ml of absolute ethanol and the solution was concentrated in vacuo to give a tan solid. 27 mg of the title compound was obtained; MS-(+)-ion: M+1=310.9 amu.

Workup

  1. customThen the excess trifluoroacetic acid was evaporated in vacuo
  2. dissolutionthe residue dissolved in 2 ml of absolute ethanol
  3. concentrationthe solution was concentrated in vacuo
  4. customto give a tan solid

Sources & evidence

ORD record
ord-13885340fea74ef78f368e4318635772
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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