Hydrochloric Acid → HCID 66874632, compound

HRID 1259060Notes

Reaction equation

HRID 1259060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[O:10]CCCC.[C:16]([Li])([CH3:19])([CH3:18])[CH3:17].[B:21](OC)([O:24]C)[O:22]C.[OH-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[C:16]([O:10][C:9]([NH:8][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[B:21]([OH:24])[OH:22])=[O:15])([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 14798Sodium HydroxideHCID 1562695Butyl (2-fluorophenyl)carbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 66874632HCID 66874632, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of Cert-butyl 2-fluorophenylcarbamate (from step 1) (1.0 eq.) in tetrahydrofuran (0.25 M) at −78° C. under N2 atmosphere was added dropwise 1.7 M tert-butyllithium (2.4 eq.). The reaction was warmed to −40° C. slowly over 2 hours, and neat trimethyl borate (3.8 eq.) was added. The reaction was warmed to room temperature over 30 minutes. An aqueous solution of 1N NaOH was slowly added to the reaction and stirred for 15 minutes. The mixture was poured into ethyl acetate and acidified with 3N HCl to dissolve the solids. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The resulting solids were stirred in 1:1 ether/hexane, filtered, and dried. The solids were carried onto the next step without further purification.

Workup

  1. temperatureThe reaction was warmed to room temperature over 30 minutes
  2. dissolutionto dissolve the solids
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vacuo
  7. stirringThe resulting solids were stirred in 1:1 ether/hexane
  8. filtrationfiltered
  9. customdried
  10. customThe solids were carried onto the next step without further purification

Sources & evidence

ORD record
ord-24e346b62aaa4739a034e57c549fd0c3
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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