2-Oxazolidinone → HCID 66608222, compound

HRID 1810585Notes

Reaction equation

HRID 1810585 reaction equation
[CH2:1]([NH:8][C:9](=[O:33])[N:10]([CH2:31][CH3:32])[CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1B1OC(C)(C)C(C)(C)O1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:35]1[CH:36]=[C:37]([C@H:42]([CH3:58])[C:43](N2[C@H](C)[C@H](C3C=CC=CC=3)OC2=O)=[O:44])[CH:38]=[C:39]([Cl:41])[CH:40]=1.[O:59]1CCNC1=O>>[CH2:1]([NH:8][C:9](=[O:33])[N:10]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[C:35]1[CH:40]=[C:39]([Cl:41])[CH:38]=[C:37]([CH:42]([CH3:58])[C:43]([OH:44])=[O:59])[CH:36]=1)[CH2:31][CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 739492-OxazolidinoneHCID 58148924HCID 58148924, compoundHCID 666071263-Benzyl-1-ethyl-1-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-urea

Product 1

HCID 66608222HCID 66608222, compound

Procedure

Prepared according to the procedure described in Example 1, Step 4, using the following starting materials: 3-benzyl-1-ethyl-1-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-urea and (4R,5S)-3-[(S)-2-(3-bromo-5-chloro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one; under the coupling conditions, the oxazolidinone was hydrolyzed to the acid and the stereocenter racemized. M+H is 519.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-01b57b6dab38479d961d1f44d8f1d63e
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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