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

HRID 735594Notes

Reaction equation

HRID 735594 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 57842704HCID 57842704, compound

Product 1

HCID 57842792(S)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidYield 70%

Procedure

Using a procedure analogous to that used to prepare 6D, 34D (800 mg, 1.37 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 34E (530 mg, 70%) as an oily brown solid. 1H NMR (400 MHz, MeOD) δ ppm 1.16 (t, J=7.20 Hz, 3 H) 2.36 (s, 3 H) 2.67-2.85 (m, 2 H) 3.01 (t, J=7.07 Hz, 2 H) 4.06 (q, J=7.16 Hz, 2 H) 4.31 (t, J=7.07 Hz, 2 H) 4.96-5.11 (m, J=12.55, 12.55, 12.55 Hz, 3 H) 6.99 (d, J=7.33 Hz, 1 H) 7.15-7.25 (m, J=7.83, 7.83 Hz, 3 H) 7.31 (s, H) 7.35-7.43 (m, 3 H).

Sources & evidence

ORD record
ord-056d74fb154040a0894c913d1338441e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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