Trifluoroacetic acid → HCID 89812894, compound

HRID 1480940Notes

Reaction equation

HRID 1480940 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@@H:16]([CH2:20][NH:21][C:22]([C:24]1[N:25]=[CH:26][C:27]2[C:32]([C:33]=1[OH:34])=[CH:31][CH:30]=[C:29]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:28]=2)=[O:23])[C:17]([OH:19])=[O:18])=O)(C)(C)C>C(Cl)Cl>[NH2:15][C@@H:16]([CH2:20][NH:21][C:22]([C:24]1[N:25]=[CH:26][C:27]2[C:32]([C:33]=1[OH:34])=[CH:31][CH:30]=[C:29]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:28]=2)=[O:23])[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89813015HCID 89813015, compound

Product 1

HCID 89812894HCID 89812894, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.4 mL) was added to a mixture of 2-(S)-tert-Butoxycarbonylamino-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid (99 mg, 0.21 mmol) in CH2Cl2 (2 mL). The resultant mixture was stirred at room temperature for 3 h and concentrated. Residue was taken up with water (100 mL) and the pH was adjusted by 1 N NaOH aq. Solution to 9-10, then acidified by 1 N HCl to pH=5. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 58 mg (0.158 mmol) in 75% yield. LC-MS ESI−: 366.10 (M−1)−.

Workup

  1. concentrationconcentrated
  2. customPrecipitate was collected
  3. washrinsed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1d9d7644cea14d5190ae11dbcdd9bf13
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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