Sodium Hydroxide → 4-(4-(3-Cyano-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

HRID 735510Notes

Reaction equation

HRID 735510 reaction equation
B(C1C=CC(CCCC(O)=O)=CC=1)(O)O.[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([B:41]3[O:46]CC(C)(C)C[O:42]3)=[CH:37][CH:36]=2)[CH:21]=[CH:22][C:23]=1[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])#[N:17].[OH-].[Na+]>>[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([B:41]([OH:42])[OH:46])=[CH:39][CH:40]=2)[CH:21]=[CH:22][C:23]=1[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])#[N:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 578425984-(4-Boronophenyl)butanoic acidHCID 57842872N-(3-Cyano-4-(isopropylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamide

Product 1

HCID 578426054-(4-(3-Cyano-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidYield 95.1%

Procedure

Using a procedure analogous to that used to prepare 2B, 9D (625 mg, 1.29 mmol) was reacted with NaOH to give 9E (508 mg, 95%) as a brown foam. MS (ESI) m/z 413.2 (M−H)−.

Sources & evidence

ORD record
ord-fcaa447d270c48a19f837e8f95a9b8f6
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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