4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → (S)-4-(2-(3-(1-(benzyloxycarbonylamino)ethyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid

HRID 735650Notes

Reaction equation

HRID 735650 reaction equation
C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:42]1[CH:43]=[C:44]([NH:48][C:49]([O:51][CH2:52][CH2:53][C:54]2[CH:59]=[CH:58][C:57](Br)=[CH:56][C:55]=2[CH3:61])=[O:50])[CH:45]=[CH:46][CH:47]=1)[CH3:41])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:42]1[CH:43]=[C:44]([NH:48][C:49]([O:51][CH2:52][CH2:53][C:54]2[CH:59]=[CH:58][C:57]([B:25]([OH:27])[OH:26])=[CH:56][C:55]=2[CH3:61])=[O:50])[CH:45]=[CH:46][CH:47]=1)[CH3:41])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 57842764(S)-4-(2-(3-(1-(benzyloxycarbonylamino)ethyl)phenylcarbamoyloxy)ethyl)-3-methylphenylbromide

Product 1

HCID 57842831(S)-4-(2-(3-(1-(benzyloxycarbonylamino)ethyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidYield 22%

Procedure

Using a procedure analogous to that used to prepare 6D, 59C (2.46 g, 4.8 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 59D (560 mg, 22%) as a solid. 1H NMR (400 MHz, MeOD-d4) δ ppm 1.25-1.41 (m, J=4.39 Hz, 3 H) 2.27 (s, 3 H) 2.61 (s, 2 H) 2.92 (s, 2 H) 4.22 (s, 2 H) 4.64 (s, 1 H) 6.84-7.56 (m, 12 H).

Sources & evidence

ORD record
ord-1df3b410b3774ab18886f6f3c2dcff15
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…