Tetrahydrofuran → HCID 58727973, compound

HRID 1992221Notes

Reaction equation

HRID 1992221 reaction equation
C1C[O:4][CH2:3]C1.[NH2:6][C:7]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([F:17])[C:8]=1[C:9]([OH:11])=[O:10].CCN(C(C)C)C(C)C.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O.C(#N)C>[F:17][C:12]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]2[NH:6][C:3](=[O:4])[O:16][C:15]2=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58728611HCID 58728611, compound

Product 1

HCID 58727973HCID 58727973, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a THF solution of 2-amino-6-fluoro-3-hydroxybenzoic acid (520 mg, 3.04 mmole) and n,n-diisopropylethylamine (942 mg, 7.29 mmole) was added bis(trichloromethyl) carbonate (1.08 g, 3.64 mmole) and stirred. Removal of solvent under vacuum afforded a residue, which was run on reversephase flash chromatography 10 to 90% acetonitrile water (0.01% TFA). The resulting fractions were evaporated.

Workup

  1. customRemoval of solvent under vacuum
  2. customafforded a residue, which
  3. customThe resulting fractions were evaporated

Sources & evidence

ORD record
ord-c982eaab94724d82a11b40dd6794a7c3
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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