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Trifluoroacetic acid → HCID 86759799, compound

HRID 965903
Notes
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Reaction equation

HRID 965903 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-05babf08d5024677948b68f8b40df5a5
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes