Diisopropylamine → HCID 178519847, compound

HRID 2075718Notes

Reaction equation

HRID 2075718 reaction equation
N(C(C)C)C(C)C.C([Li])CCC.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[SH:18].[F:19][C:20]([F:27])([F:26])[C:21](OCC)=[O:22]>C1COCC1>[F:19][C:20]([F:27])([F:26])[C:21]([C:17]1[S:13][C:14]([SH:18])=[N:15][CH:16]=1)=[O:22]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 9794Ethyl trifluoroacetateHCID 178418339ButyllithiumHCID 178527881HCID 178527881, compound

Product 1

HCID 178519847HCID 178519847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

iPr2NH (1.0 g, 9.4 mmol) was dissolved in THF (12 mL) and cooled to −10° C. n-Butyllithium (2.5M, 3.8 mL, 9.4 mmol) was added dropwise, and the reaction was cooled to −78° C. Thiazole-2-thiol (1.0 g, 8.5 mmol) in THF (2.5 mL) was added, followed by ethyl trifluoroacetate (1.3 mL, 11.1 mmol), and the reaction was stirred at −78° C. for 1 hours. The reaction was warmed to −10° C. and quenched with 5% aqueous NH4Cl (10 mL). The aqueous layer was acidified and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 10a.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to −10° C.
  3. customquenched with 5% aqueous NH4Cl (10 mL)
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cb69e9826e4d41a7ac0fcb10ad7e598f
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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