Pivaloyl chloride → HCID 24782853, compound

HRID 1019601Notes

Reaction equation

HRID 1019601 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([CH3:17])=[C:14](Br)[S:15][C:9]=2[CH2:8][CH2:7]1)=O)C.C([Li])CCC.[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26]>C1COCC1>[CH3:23][C:24]([CH3:29])([CH3:28])[C:25]([C:14]1[S:15][C:9]2[CH2:8][CH2:7][NH:6][CH2:12][CH2:11][C:10]=2[C:13]=1[CH3:17])=[O:26]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 58256118HCID 58256118, compoundHCID 178418339Butyllithium

Product 1

HCID 24782853HCID 24782853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product of step (h) (60 mg, 0.19 mmol) was dissolve in 2 mL THF and cooled to −78° C. Butyl lithium (0.15 mL of 1.6M) was added and the reaction was stirred for 5 minutes. Trimethylacetyl chloride (36 uL, 0.3 mmol) was added and the reaction was warmed to room temperature. The reaction was quenched with water (5 mL) and the product was extracted into DCM (2×). The extracts were concentrated to dryness and treated with 4 mL of 1:1 EtOH:40% KOH (aq) and heated to 100° C. for 14 hours. The reaction was cooled and diluted with water. The product was extracted into DCM (2×5 mL). The extracts were concentrated and the title compound was purified by preparative HPLC-MS. 1H NMR (CD3OD) δ 3.38-3.31 (m, 4H), 3.23 (t, J=5.1 Hz, 2H), 3.04 (t, J=5.2 Hz, 2H), 2.30 (s, 3H), 1.32 (s, 9H); MS: ESI (positive): 252 (M+H).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. customThe reaction was quenched with water (5 mL)
  3. extractionthe product was extracted into DCM (2×)
  4. concentrationThe extracts were concentrated to dryness
  5. additiontreated with 4 mL of 1:1 EtOH
  6. temperature40% KOH (aq) and heated to 100° C. for 14 hours
  7. temperatureThe reaction was cooled
  8. additiondiluted with water
  9. extractionThe product was extracted into DCM (2×5 mL)
  10. concentrationThe extracts were concentrated
  11. customthe title compound was purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-a857303fcb5f4ae58056c85b13b53d04
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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