Propionyl chloride → HCID 11357456, compound

HRID 2392838Notes

Reaction equation

HRID 2392838 reaction equation
[CH2:1]([C@H:8]1[C:12]([CH3:14])([CH3:13])[O:11][C:10](=[O:15])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:21](Cl)(=[O:24])[CH2:22][CH3:23]>O1CCCC1>[O:24]=[C:21]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]([CH3:13])([CH3:14])[O:11][C:10]1=[O:15])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 10921652(4S)-4-Benzyl-5,5-dimethyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 11357456HCID 11357456, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of the auxiliary (10) (0.8 g, 3.90 mmol) in solution in tetrahydrofuran (27 ml) at -78° C. with butyllithium (1.3M, 3.03 ml, 3.94 mmol) and propionyl chloride (0.373 ml, 4.29 mmol) for 30 minutes and then at room temperature overnight with work-up and recrystallisation from pentane gave the title compound (20) as a solid (0.870 g, 85%); mp 61° C.; νmax (CHCl3) 1773 and 1702 cm-1 ; [α]D25 (c 1 in CHCl3)=-42.5; (Found: C, 69.06; H, 7.43; N, 5.21. C15H19NO3 requires C, 68.94; H, 7.33; N, 5.36%); δH (CDCl3 ; 200 MHz) 1.13 (3H, t, J=7.36, CH2CH3), 1.35 (3H, s, C(CH3)2), 1.36 (3H, s, C(CH3)2), 2.81-2.98 (2H, m, CH2Ph and CH2CH3), 3.14 (1H, dd, J=4.0 and 14.4, CH2Ph), 4.50 (1H, dd, J=4.0 and 9.6, CHCH2), 7.18-7.34 (5H, m, ArCH); δC (125 MHz; CDCl3) 8.20 (CH3), 22.15 (CH3), 28.43 (CH3), 29.23 (CH2), 35.24 (CH2), 63.46 (CH), 82.20 (C), 126.96 (CH), 128.82 (CH), 129.26 (CH), 137.26 (C), 152.93 (CO), 174.53 (CO); m/z (CI+, NH3) 262 (M+ +1).

Workup

  1. customat room temperature overnight with work-up and recrystallisation from pentane

Sources & evidence

ORD record
ord-7bb3903a09ae47b184bcb41f13b433f5
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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