Trifluoroacetic acid → Water TFA acetonitrile

HRID 1599918Notes

Reaction equation

HRID 1599918 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].FC(F)(F)C(O)=[O:11].[NH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:43]=[CH:42][C:23]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])[C:29]([OH:31])=[O:30])=[O:25])=[CH:22][CH:21]=1.[OH-].[Na+].Cl.[CH:47](=N)[O:48]C(C)C>O>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[OH2:11].[CH3:17][C:16]#[N:15].[CH:47]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][S:33]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)(=[O:35])=[O:34])[C:29]([OH:31])=[O:30])=[O:25])=[CH:42][CH:43]=1)=[O:48]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium Hydroxide2×HCID 12801779Propan-2-yl methanimidate--hydrogen chloride (1/1)HCID 86752440HCID 86752440, compound

Product 2

HCID 22145617Water TFA acetonitrileYield 0.1%HCID 86752441HCID 86752441, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The TFA salt 9-1 (80 mg, 0.19 mmol) was dissolved in water at 0° and the pH of the solution was adjusted to 9 by addition of 1N NaOH. Isopropyl formimidate hydrochloride (130 mg, 0.95 mmol) was added in two portions 10 min apart maintaining pH 9 with additional 1N NaOH. After 60 rain at 0° the reaction was warmed to RT for 90 min, then lyophylized. Preparative HPLC (C-18, 0.1% TFA H2O/CH3CN) provided 9-2 as a white solid.

Sources & evidence

ORD record
ord-e40444c7341945979b5fadd5b4e38f09
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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