4-Benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one → (S)-4-Benzyl-3-[(R)-2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one

HRID 1692093Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH2:30]([O:37][C:38]1[CH:39]=[C:40]([Cl:47])[C:41]([CH2:45]Br)=[C:42]([Cl:44])[CH:43]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@@H:15]([CH2:45][C:41]1[C:40]([Cl:47])=[CH:39][C:38]([O:37][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:43][C:42]=1[Cl:44])[CH2:16][CH:17]=[CH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve 4-Benzyl-3-pent-4-enoyl-oxazolidin-2-one (2.21 g, 8.52 mmol) in 25 ml of dry THF. Chilled to −78° C. Add LiN(TMS)2 (10.23 ml, 10.23 mmol). Stir for 30 min at same temperature. Add 5-Benzyloxy-2-bromomethyl-1,3-dichloro-benzene (3.10 g, 8.95 mmol) in 5 ml of THF. Let the reaction slowly warm to room temperature.

Workup

customthe reaction
temperatureslowly warm to room temperature

Sources & evidence

ORD record: ord-b95a392fc67a46618b6465454907f492
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153807B2

Reaction notes

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