Trifluoroacetic acid → HCID 71737071, compound

HRID 1481093Notes

Reaction equation

HRID 1481093 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][NH:14][C:15]([C:17]1[N:18]=[C:19]([C:35]#[N:36])[C:20]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:23]=[C:22]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=2)=[O:16])[C:10]([OH:12])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:13][NH:14][C:15]([C:17]1[N:18]=[C:19]([C:35]#[N:36])[C:20]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:23]=[C:22]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=2)=[O:16])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71737070HCID 71737070, compound

Product 1

HCID 71737071HCID 71737071, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(S)-tert-butoxycarbonylamino-3-[(1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid (90 mg, 0.18 mmol) in CH2Cl2 (2 mL) was added TFA (0.5 mL). The resultant mixture was stirred at room temperature for 4 h. Reaction mixture was concentrated and residue was treated with water (80 mL). The pH value was adjusted to 9-10 by 1 N NaOH aq. Solution. Then it was acidified by 1 N HCl to pH=4-5. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 57 mg (0.15 mmol) in 81% yield. LC-MS ESI−: 391.08 (M−1)−.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additionresidue was treated with water (80 mL)
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3be005f7a75141b79ccfe6fce0ce12f2
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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