4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → 4-(2-(3-Cyano-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid
Reaction equation
C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.[C:29]([C:31]1[CH:32]=[C:33]([NH:42][C:43](=[O:55])[O:44][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50](Br)=[CH:49][C:48]=2[CH3:54])[CH:34]=[CH:35][C:36]=1[S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])#[N:30]>>[C:29]([C:31]1[CH:32]=[C:33]([NH:42][C:43]([O:44][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([B:25]([OH:27])[OH:26])=[CH:49][C:48]=2[CH3:54])=[O:55])[CH:34]=[CH:35][C:36]=1[S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])#[N:30]Participants
3
Procedure
Using a procedure analogous to that used to prepare 6D, 31A (745 mg, 1.66 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 31B (468 mg, 68%) as a tan foam. 1H NMR (400 MHz, MeOD) δ ppm 1.25 (t, J=7.33 Hz, 3 H) 2.34-2.40 (m, 3 H) 3.03 (t, J=6.95 Hz, 2 H) 3.35 (q, J=7.33 Hz, 2 H) 4.39 (t, J=7.07 Hz, 2 H) 7.20 (d, J=7.33 Hz, 1 H) 7.30-7.43 (m, 2 H) 7.86 (dd, J=8.84, 1.77 Hz, 1 H) 7.99 (d, J=8.84 Hz, 1 H) 8.11 (d, J=2.02 Hz, 1 H) 10.05 (s, 1 H).
Sources & evidence
- ORD record
- ord-e26bfb040621468aa2a757f31f549783
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592331B2
Reaction notes
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