2-Thiopheneboronic acid → tert-butyl (2R)-2-hydroxy-2-[(2R)-4-[4-(2-methylsulfonylphenyl)phenyl]-3-oxomorpholin-2-yl]acetate

HRID 876609Notes

Reaction equation

HRID 876609 reaction equation
[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=2)[C:11]1=[O:23])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)(=[O:27])=[O:26].S1C=CC=C1B(O)O>>[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:25]([CH3:24])(=[O:27])=[O:26])=[CH:18][CH:17]=2)[C:11]1=[O:23])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 27339602-Thiopheneboronic acidHCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 67223457HCID 67223457, compound

Product 1

HCID 67223107tert-butyl (2R)-2-hydroxy-2-[(2R)-4-[4-(2-methylsulfonylphenyl)phenyl]-3-oxomorpholin-2-yl]acetateYield 79.8%

Procedure

According to the Step 22-1 in synthetic method for EXAMPLE 22, compound 105-1 (0.12 g) and 2-methylsulfonylphenylboronic acid (0.11 g) were used instead of 14-4 and 2-thiopheneboronic acid to obtain compound 105-2 (102 mg) as yellow oil.

Sources & evidence

ORD record
ord-3daefd2031134eb5a57deac97f37bff8
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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