Hydrochloric Acid → HCID 50923243, compound

HRID 1798268Notes

Reaction equation

HRID 1798268 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:28][C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[CH:14]=[C:15]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[C:24]([O:23][C:21]([NH:20][CH2:19][CH2:18][CH2:17][O:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:35])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:28][C:29]2[CH:34]=[N:33][CH:32]=[CH:31][N:30]=2)[CH:14]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292875HCID 58292875, compound

Product 1

HCID 50923243HCID 50923243, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of [4-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (4 mg) in THF/H2O (1 mL, 1:1) was treated with LiOH (1.4 mg) at 0° C. and the reaction was stirred at room temperature for 2 h. The mixture was acidified to pH 3 with 1N HCl and purified by preparative HPLC to give the title compound (1.5 mg) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.40 (s, 1H), 8.28-8.27 (m, 1H), 8.14-8.13 (m, 1H), 6.93 (d, J=1.8 Hz, 1H), 6.87 (d, J=1.8 Hz, 1H), 5.63-5.59 (m, 1H), 4.05 (t, 2H), 3.23-3.20 (m, 2H), 3.18-3.16 (m, 1H), 2.39-2.31 (m, 1H), 1.96 (t, 2H), 1.40 (s, 9H). MS calcd for (C21H26BN3O8+H-Boc)+: 360.2. MS found: (M+H-Boc)+=360.2.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8ce4b39b48484f3cab1ef8bb571227eb
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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