Triethylamine → HCID 22184675, compound

HRID 1795069Notes

Reaction equation

[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](O)=[O:15])[CH2:9][CH2:8]1)([CH3:3])[CH3:2].C(Cl)(=O)C(C)(C)C.C(N(CC)CC)C.[Cl-].[Li+].[C:39]1([CH2:45][CH:46]2[CH2:50][O:49][C:48](=[O:51])[NH:47]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[C:39]1([CH2:45][CH:46]2[CH2:50][O:49][C:48](=[O:51])[N:47]2[C:14](=[O:15])[CH2:13][CH:10]2[CH2:11][CH2:12][CH:7]([CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:17]([CH3:19])[CH3:18])[CH:20]([CH3:21])[CH3:22])[CH2:8][CH2:9]2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

Reactant 5

HCID 8471Triethylamine

HCID 62493Pivaloyl chloride

HCID 433294Lithium Chloride

HCID 5596684-Benzyl-1,3-oxazolidin-2-one

HCID 22184655HCID 22184655, compound

Product 1

HCID 22184675HCID 22184675, compound

Procedure

The acid (8.5 g, 25.9 mmol) from step F was treated with 3.14 g (3.2 mL, 26 mmol) of pivaloyl chloride and 10.5 g (14.5 mL, 26 mmol) of triethylamine followed by 1.32 g (28 mmol) of lithium chloride and 4.60 g (26 mmol) of 4-phenylmethyl-2-oxazolidinone according to the procedure of G.-J. Ho and D. J. Mathre, J. Org. Chem. 1995, 60, 2271–2273 to provide, after purification by flash chromatography on silica gel (10% ethyl acetate/hexane), 11.5 g (91%) of the title compound. 1H NMR (500 MHz, CDCl3) δ 7.32 (m, 2H), 7.27 (m, 1H), 7.23 (d, 2H, J=6.9 Hz), 5.31 (m, 1H),

Workup

custom1995, 60, 2271–2273 to provide
customafter purification by flash chromatography on silica gel (10% ethyl acetate/hexane), 11.5 g (91%) of the title compound

Sources & evidence

ORD record: ord-43fe6f3d3f304a37aa99f0f77bec7dab
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026316B2

Reaction notes

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