Water → 2-Cyclopropyl-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

HRID 1481214Notes

Reaction equation

HRID 1481214 reaction equation
C([O:5][C:6](=[O:33])[CH:7]([CH:30]1[CH2:32][CH2:31]1)[CH2:8][NH:9][C:10]([C:12]1[N:13]=[CH:14][C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[C:17]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:16]=2)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH:30]1([CH:7]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[CH:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[C:17]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=3)=[O:11])[C:6]([OH:33])=[O:5])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 898131072-Cyclopropyl-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid tert-butyl ester

Product 1

HCID 717367412-Cyclopropyl-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-cyclopropyl-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester (52 mg) and TFA (2 mL) in DCM (2 mL) was stirred at rt for 3 h; then the mixture was concentrated and resulting residue was treated with water; the solids were collected via filtration and air dried to give desired product as white solids (37 mg). LC-MS ESI+: 393 (M+1)+.

Workup

  1. concentrationthen the mixture was concentrated
  2. customresulting residue
  3. filtrationthe solids were collected via filtration and air
  4. customdried

Sources & evidence

ORD record
ord-fb8a62ff947e435c996cf891fb991297
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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