Imidazole → HCID 59279555, compound

HRID 1098158Notes

Reaction equation

[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[OH:9][C@@H:10]([CH2:15][O:16][C@H:17]([CH3:21])[CH2:18][O:19][CH3:20])[C:11]([O:13][CH3:14])=[O:12].N1C=CN=C1>CN(C=O)C>[Si:5]([O:9][C@@H:10]([CH2:15][O:16][C@H:17]([CH3:21])[CH2:18][O:19][CH3:20])[C:11]([O:13][CH3:14])=[O:12])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 40 °C

Procedure

tert-Butylchlorodimethylsilane (7.09 g, 47.01 mmol) was added to (S)-methyl 2-hydroxy-3-((R)-1-methoxypropan-2-yloxy)propanoate (Intermediate Y6) (7.53 g, 39.18 mmol) and 1H-imidazole (5.33 g, 78.35 mmol) in DMF (50 mL) at room temperature under nitrogen. The resulting solution was stirred at 40° C. for 5 hours. The reaction mixture was evaporated to dryness and re-dissolved in ethyl acetate (125 mL), and washed sequentially with water (50 mL) and saturated brine (25 mL). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 50% ethyl acetate in isohexane to afford the product (2.58 g, 21.5%). 1H NMR (400 MHz, DMSO) δ −0.01 (d, 6H), 0.81 (s, 9H), 0.97 (d, 3H), 3.13-3.29 (m, 5H), 3.49-3.64 (m, 6H), 4.26-4.31 (m, 1H); m/z (ESI+) M-C4H9=249; GC tR=10.92 min.

Workup

customThe reaction mixture was evaporated to dryness
dissolutionre-dissolved in ethyl acetate (125 mL)
washwashed sequentially with water (50 mL) and saturated brine (25 mL)
dry with materialThe organic layer was dried (MgSO4)
customevaporated
customThe crude product was purified by flash silica chromatography
washeluting with 0 to 50% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-0a4282c5ef124615a5d263efdf7f29fc
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143263B2

Reaction notes

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