Boronic Acid → HCID 57842682, compound

HRID 735520Notes

Reaction equation

HRID 735520 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]([OH:27])[OH:26])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])#[N:2].BrC1C=CC(CCCC(NC2C=CC(S(CC)(=O)=O)=C(C=2)CN[C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=O)=CC=1.CC1(C)COB(B2OCC(C)(C)CO2)OC1.B(O)O>>[C:51]([O:50][C:49]([NH:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([B:25]([OH:26])[OH:27])=[CH:23][CH:24]=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[O:55])([CH3:54])([CH3:53])[CH3:52]

Participants

5

Reactant 4

HCID 61668Boronic AcidHCID 2734316Bis(neopentyl glycolato)diboronHCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 57842758tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzylcarbamate

Product 1

HCID 57842682HCID 57842682, compoundYield 82%

Procedure

Using a procedure analogous to that used to prepare 6D, 15B (0.541 g, 1.0 mmol) was coupled to 5,5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl](0.249 g, 1.1 mmol) and then hydrolyzed to the free boronic acid to give 15C (334 mg, 82%) as a peach colored foam. MS (ESI) m/z 505.03 (M+H)+.

Sources & evidence

ORD record
ord-985f94c5ebf848e6b030595cc957d660
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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