Pivaloyl chloride → HCID 24782853, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 μL, 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);
Workup
- temperaturethe reaction was warmed to room temperature
- customThe reaction was quenched with water (5 mL)
- extractionthe product was extracted into DCM (2×)
- concentrationThe extracts were concentrated to dryness
- additiontreated with 4 mL of 1:1 EtOH
- temperature40% KOH (aq) and heated to 100° C. for 14 hours
- temperatureThe reaction was cooled
- additiondiluted with water
- extractionThe product was extracted into DCM (2×5 mL)
- concentrationThe extracts were concentrated
- customthe title compound was purified by preparative HPLC-MS
Sources & evidence
- ORD record
- ord-1cb2fbe7a90b4bbab05b948cc3455a76
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893051B2
Reaction notes
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