Sodium Azide → (4-Azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

HRID 1798253Notes

Reaction equation

HRID 1798253 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH2:16]Br)[C:7]1=2)[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CC#N.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH2:16][N:20]=[N+:21]=[N-:22])[C:7]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58292861(4-Bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58292573(4-Azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a crude (4-bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester in CH3CN/H2O (10/2 mL) was added sodium azide (3.1 g, 48 mmol). The solution was stirred overnight at r.t. The crude solution was purified by HPLC, yielded 450 mg of the title compound. 1H NMR (300 MHz, CD3CN) δ 7.21 (s, 1H), 6.99 (s, 1H), 5.61 (dd, 1H), 4.31-4.56 (dd, 2H), 4.10 (q, 2H), 3.02-3.14 (dd, 1H), 2.37-2.43 (m, 1H), 1.21 (t, 3H).

Workup

  1. customThe crude solution was purified by HPLC

Sources & evidence

ORD record
ord-f15f6739d0a24be48f012e1c1c4ed8f5
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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