Sodium Hydroxide → 4-(4-(4-(tert-Butylsulfonyl)-3-cyanophenylamino)-4-oxobutyl)phenylboronic acid

HRID 735515Notes

Reaction equation

HRID 735515 reaction equation
B(C1C=CC(CCCC(O)=O)=CC=1)(O)O.[C:16]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:48])[CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([B:40]3[O:45]CC(C)(C)C[O:41]3)=[CH:36][CH:35]=2)=[CH:25][C:24]=1[C:49]#[N:50])(=[O:22])=[O:21])([CH3:19])([CH3:18])[CH3:17].[OH-].[Na+]>>[C:16]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:48])[CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([B:40]([OH:41])[OH:45])=[CH:38][CH:39]=2)=[CH:25][C:24]=1[C:49]#[N:50])(=[O:22])=[O:21])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 578425984-(4-Boronophenyl)butanoic acidHCID 57842633N-(4-(tert-butylsulfonyl)-3-cyanophenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamide

Product 1

HCID 578427684-(4-(4-(tert-Butylsulfonyl)-3-cyanophenylamino)-4-oxobutyl)phenylboronic acidYield 71%

Procedure

Using a procedure analogous to that used to prepare 2B, 10D (431 mg, 0.869 mmol) was reacted with NaOH to give 10E (263 mg, 71%) as a brown solid. 1H NMR (400 MHz, THF-d8) δ 1.34 (s, 9 H), 1.96-2.07 (m, 2 H), 2.35 (t, J=7.25 Hz, 2 H), 2.69 (t, J=7.25 Hz, 2 H), 7.09 (s, 1 H), 7.16 (d, J=7.91 Hz, 2 H), 7.71 (d, J=8.35 Hz, 2 H), 7.92-7.96 (m, 1 H), 8.01 (dd, J=2.20 Hz, 1 H), 8.23 (d, J=2.20 Hz, 1 H), 9.69-9.77 (m, 1 H).

Sources & evidence

ORD record
ord-99361ccf4b8d47eb91e45116e883a7f2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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