Dimethylformamide → Trifluoroacetic acid

HRID 50113Notes

Reaction equation

HRID 50113 reaction equation
[F:1][C:2]([F:11])([F:10])C1C=CN=C(S)C=1.[C:12]([O-:15])([O-])=[O:13].[K+].[K+].CN(C=[O:22])C>CC#N>[C:12]([OH:15])([C:2]([F:11])([F:10])[F:1])=[O:13].[OH2:22].[C:12]([OH:15])([C:2]([F:11])([F:10])[F:1])=[O:13]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 178506236HCID 178506236, compound

Product 2

HCID 6422Trifluoroacetic acidYield 23%HCID 22392675Trifluoroacetic acid waterYield 0.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Glucose-C6-2-mesitylenesulfonated vancomycin TFA salt (XLI) (10 mg, 0.00573 mmol), 4-(trifluoromethyl)-2-pyridinethiol (21.6 mg 0.12 mmol), and K2CO3 (17 mg 0.123 mmol), are dissolved with dry DMF (0.5 mL). The mixture is stirred at 65° C. After 2 h. analytical HPLC indicates the reaction is done. The mixture is filtered and purified by ODS-HPLC (LUNA 5 μm C18(2), 21.2×250 mm, UV=285 nm, A: 0.1% TFA/H2O, B: MeCN, 0-50-100% B 0-30-40 min., 8 mL/min, tr=35 min.) to give (LX) as a white amorphous TFA salt (2.3 mg, 0.00133 mmol, 23%). LRESI-MS 1613 (M+4H, for C71H8035Cl2F3N11O23S)+, 1143 (M−vancosamine-glucose+H)+.

Workup

  1. filtrationThe mixture is filtered
  2. custompurified by ODS-HPLC (LUNA 5 μm C18(2), 21.2×250 mm, UV=285 nm

Sources & evidence

ORD record
ord-f1706b69fd514405b76b24f255da13b2
Source dataset
uspto-grants-2004_03
Patent number
US06710168B1

Reaction notes

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