(4R,5S)-4-methyl-5-phenyl-3-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionyl}-oxazolidin-2-one → (3-Methyl-5-{4'-[1-methyl-2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-biphenyl-4-yl}-isoxazol-4-yl)-carbamic acid (R)-1-(2-chloro-phenyl)-ethyl ester

HRID 553732Notes

Reaction equation

HRID 553732 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:32])[CH:15]([C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)[CH3:16].[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C@H:40]([O:42][C:43](=[O:58])[NH:44][C:45]1[C:46]([CH3:57])=[N:47][O:48][C:49]=1[C:50]1[CH:55]=[CH:54][C:53](Br)=[CH:52][CH:51]=1)[CH3:41]>>[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C@H:40]([O:42][C:43](=[O:58])[NH:44][C:45]1[C:46]([CH3:57])=[N:47][O:48][C:49]=1[C:50]1[CH:55]=[CH:54][C:53]([C:20]2[CH:19]=[CH:18][C:17]([CH:15]([CH3:16])[C:14]([N:3]3[C@H:2]([CH3:1])[C@H:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:5][C:4]3=[O:13])=[O:32])=[CH:22][CH:21]=2)=[CH:52][CH:51]=1)[CH3:41]

Participants

3

Reactant 2

HCID 58539564(4R,5S)-4-methyl-5-phenyl-3-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionyl}-oxazolidin-2-oneHCID 66660466(R)-1-(2-chlorophenyl)ethyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate

Product 1

HCID 67351133(3-Methyl-5-{4'-[1-methyl-2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-biphenyl-4-yl}-isoxazol-4-yl)-carbamic acid (R)-1-(2-chloro-phenyl)-ethyl ester

Procedure

Diastereomer B—Prepared as described in Example 36, Step 6 using (4R,5S)-4-methyl-5-phenyl-3-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionyl}-oxazolidin-2-one (Diastereomer B) and [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-chloro-phenyl)-ethyl ester.

Sources & evidence

ORD record
ord-abe887cff36748cba6dca7f296612fd9
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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