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

HRID 735614Notes

Reaction equation

HRID 735614 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:47]1[CH:52]=[CH:51][CH:50]=[C:49]([NH:53][C:54]([O:56][CH2:57][CH2:58][C:59]2[CH:64]=[CH:63][C:62](Br)=[CH:61][C:60]=2[CH3:66])=[O:55])[CH:48]=1)[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[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:47]1[CH:48]=[C:49]([NH:53][C:54]([O:56][CH2:57][CH2:58][C:59]2[CH:64]=[CH:63][C:62]([B:25]([OH:27])[OH:26])=[CH:61][C:60]=2[CH3:66])=[O:55])[CH:50]=[CH:51][CH:52]=1)[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[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 57842714(R)-ethyl 3-(benzyloxycarbonylamino)-3-(3-((4-bromo-2-methylphenethoxy)carbonylamino)phenyl)propanoate

Product 1

HCID 57842846(R)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidYield 64%

Procedure

Using a procedure analogous to that used to prepare 6D, 39D (1.07 g, 1.84 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 39E (640 mg, 64%) as a tan foam. 1H NMR (400 MHz, CD3OD) δ ppm 1.14 (t, J=7.15 Hz, 3 H) 2.65-2.86 (m, 2 H) 2.99 (t, J=7.15 Hz, 2 H) 4.05 (q, J=7.15 Hz, 2 H) 4.19-4.35 (m, 2 H) 4.93-5.14 (m, 3 H) 6.98 (d, J=7.70 Hz, 1 H) 7.12-7.33 (m, 8 H) 7.34-7.45 (m, 2 H) 7.45-7.59 (m, 1 H) 9.14 (s, 1 H)

Sources & evidence

ORD record
ord-e702661202fd43758f9e0fea9064ddce
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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