2-Thiopheneboronic acid → (2R)-2-hydroxy-2-[(2R)-4-[4-[2-(2-hydroxyethyl)phenyl]phenyl]-3-oxomorpholin-2-yl]-N-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]acetamide

HRID 876610Notes

Reaction equation

HRID 876610 reaction equation
[OH:1][C@H:2]([C@H:18]1[O:23][CH2:22][CH2:21][N:20]([C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)[C:19]1=[O:31])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15](=[O:17])[O:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4].CC([Si](C)(C)[O:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O)(C)C.S1C=CC=C1B(O)O>>[OH:1][C@H:2]([C@H:18]1[O:23][CH2:22][CH2:21][N:20]([C:24]2[CH:29]=[CH:28][C:27]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[CH2:39][CH2:38][OH:37])=[CH:26][CH:25]=2)[C:19]1=[O:31])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15](=[O:17])[O:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 3

HCID 27339602-Thiopheneboronic acidHCID 441193492-(2-(tert-Butyldimethylsilyloxy)ethyl)phenylboronic acidHCID 136337790(2R)-2-hydroxy-2-[(2R)-4-(4-iodophenyl)-3-oxomorpholin-2-yl]-N-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]acetamide

Product 1

HCID 136337789(2R)-2-hydroxy-2-[(2R)-4-[4-[2-(2-hydroxyethyl)phenyl]phenyl]-3-oxomorpholin-2-yl]-N-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]acetamideYield 33.7%

Procedure

According to the Step 22-1 in synthetic method for EXAMPLE 22, compound 106-2 (30 mg) and [2-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]phenyl]boronic acid (31.4 mg) were used instead of 14-4 and 2-thiopheneboronic acid to obtain compound 106-3 (10 mg) as a colorless amorphous solid.

Sources & evidence

ORD record
ord-3e0588d488ab4356bd3055ead7776472
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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