Trifluoroacetic acid → Trifluoroacetic acid

HRID 1481033Notes

Reaction equation

HRID 1481033 reaction equation
C(OC([NH:8][C@H:9]([CH2:13][CH2:14][NH:15][C:16]([C:18]1[N:19]=[C:20]([C:36]#[N:37])[C:21]2[C:26]([C:27]=1[OH:28])=[CH:25][CH:24]=[C:23]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:22]=2)=[O:17])[C:10]([OH:12])=[O:11])=O)(C)(C)C.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[NH2:8][C@H:9]([CH2:13][CH2:14][NH:15][C:16]([C:18]1[N:19]=[C:20]([C:36]#[N:37])[C:21]2[C:26]([C:27]=1[OH:28])=[CH:25][CH:24]=[C:23]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:22]=2)=[O:17])[C:10]([OH:12])=[O:11].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89813045(R)-2-(tert-Butoxycarbonylamino)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)butanoic acid

Product 2

HCID 6422Trifluoroacetic acidHCID 71736906(R)-2-Amino-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-(tert-Butoxycarbonylamino)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)butanoic acid (40 mg, 0.06 mmol) was dissolved in TFA (4 mL) and CH2Cl2 (4 mL). The resulting mixture was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was dissolved again in CH2Cl2 (4 mL). The volatiles were removed again in vacuo to give the title compound as its TFA salt in 19 mg. MS: (−) m/z 405.27 (M−1).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved again in CH2Cl2 (4 mL)
  3. customThe volatiles were removed again in vacuo

Sources & evidence

ORD record
ord-68f5d3936b214de58a6f32811e1ad970
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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