Pyridine → HCID 68538506, compound

HRID 1994308Notes

Reaction equation

[OH:1][CH2:2][CH:3]([NH:13][CH:14]([CH:22]([CH3:24])[CH3:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.N1C=CC=CC=1.[S:31](Cl)(Cl)=[O:32]>C(Cl)Cl>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH:3]2[CH2:2][O:1][S:31](=[O:32])[N:13]2[CH:14]([CH:22]([CH3:24])[CH3:23])[C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

t-Butyl 2-(1-hydroxymethyl-2-(4-methoxyphenyl)ethylamino)-3-methylbutyrate (2.49 g; 7.4 mmol) was dissolved in CH2Cl2 (180 ml). The reaction solution was cooled to −78° C. Then pyridine (3 ml; 37 mmol) was added and subsequently thionyl chloride (0.64 ml; 8.88 mmol) was added dropwise. The reaction mixture was stirred for 1 h, during which the temperature was allowed to reach 0° C. It was taken up in CH2Cl2 and washed with aqueous HCl (1%; 2×) and NaHCO3 solution. The organic phase was dried over Na2SO4 and concentrated in a rotary evaporator. The crude product was purified by filtration through silica gel (100 g). t-Butyl 2-(4-(4-methoxybenzyl)-2-oxo-(1,2,3)oxathiazolidin-3-yl)-3-methylbutyrate (2.35 g; 0.61 mmol) was obtained as a dark yellow oil. MS: 384.20 (M+H); Rt: 1.76 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

customto reach 0° C
washwashed with aqueous HCl (1%; 2×) and NaHCO3 solution
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in a rotary evaporator
filtrationThe crude product was purified by filtration through silica gel (100 g)

Sources & evidence

ORD record: ord-869fd0a416de4de5aac0ec5c62281cc4
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652143B2

Reaction notes

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