Trifluoroacetic acid → HCID 86759799, compound

HRID 584621Notes

Reaction equation

HRID 584621 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:33]=[CH:32][CH:31]=[CH:30][C:7]=1[O:8][CH2:9][CH:10]([OH:29])[CH2:11][N:12]1[CH2:16][C@@H:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14][C@H:13]1[C:25]([O:27]C)=[O:26])(=[O:4])[CH3:3].O.[OH-].[Li+].[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(#N)C.O>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[C:2]([NH:5][C:6]1[CH:33]=[CH:32][CH:31]=[CH:30][C:7]=1[O:8][CH2:9][CH:10]([OH:29])[CH2:11][N:12]1[CH2:16][C@@H:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14][C@H:13]1[C:25]([OH:27])=[O:26])(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 86759800HCID 86759800, compound

Product 1

HCID 86759799HCID 86759799, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Compound (i) (50 mg, 0.1 mmol) was dissolved in acetonitrile (2 ml) and water (3 ml). Lithium hydroxide hydrate (8 mg, 0.2 mmol) dissolved in water (0.5 ml) was added. The reaction was complete after 0.5 h as determined by analytical HPLC. The mixture was acidified with TFA and purified by preparative RP-HPLC using acetonitrile and water containing 0.1% TFA as mobile phase. The appropriate fraction was concentrated in vacuo and the residue lyophilized from acetic acid to give the title compound as a white amorphous solid (27 mg, 48%). The substance is a diastereomeric mixture.

Workup

  1. additionwas added
  2. custompurified by preparative RP-HPLC
  3. concentrationThe appropriate fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-ceac71932cfe4420b466f5d5e7a2c193
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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