Sodium Hydroxide → HCID 57842800, compound

HRID 735518Notes

Reaction equation

HRID 735518 reaction equation
B(C1C=CC(CCCC(O)=O)=CC=1)(O)O.CC1(C)C[O:21][B:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][O:31][C:32](=[O:42])[NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]#[N:41])[CH:35]=3)=[CH:25][CH:24]=2)[O:19]C1.[OH-].[Na+]>>[C:40]([C:36]1[CH:35]=[C:34]([NH:33][C:32]([O:31][CH2:30][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([B:20]([OH:19])[OH:21])=[CH:28][CH:27]=2)=[O:42])[CH:39]=[CH:38][CH:37]=1)#[N:41]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 57842566(3-Cyanophenyl)carbamic acid 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-phenyl]ethyl esterHCID 578425984-(4-Boronophenyl)butanoic acid

Product 1

HCID 57842800HCID 57842800, compoundYield 48%

Procedure

Using a procedure analogous to that used to prepare 2B, 11B (434 mg, 1.15 mmol) was reacted with NaOH to give 11C (170 mg, 48%) as a solid. 1H NMR (400 MHz, THF-d8) δ 2.98 (t, J=7.03 Hz, 2 H), 4.38 (t, J=6.81 Hz, 2 H), 7.10 (s, 2 H), 7.22 (d, J=7.91 Hz, 1 H), 7.30 (d, J=7.47 Hz, 1 H), 7.39 (t, J=7.91 Hz, 1 H), 7.68 (d, J=8.35 Hz, 1 H), 7.73 (d, J=8.35 Hz, 2 H), 7.87 (s, 1 H), 9.11 (s, 1 H).

Sources & evidence

ORD record
ord-628d012e0721480bad7452bf39284762
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…