Cesium carbonate → HCID 58292807, compound

HRID 1798265Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:24])[CH:14]=[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]1=2)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:24][C:33]3[CH:38]=[N:37][CH:36]=[CH:35][N:34]=3)[CH:14]=[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]1=2)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of (4-benzyloxy-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (710 mg, 2.08 mmol) and Cs2CO3 (1.36 g, 4.16 mmol) in DMF (10 mL) was treated with 2-chloropyrazine (357 mg, 3.11 mmol) at room temperature and the reaction was heated to 80° C. for 3 h. The reaction mixture was concentrated to dryness. The residue was diluted with water and adjusted pH to 3 by 1N HCl. The aqueous phase was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by preparative HPLC to afford the title compound (410 mg, 50%). MS calcd for (C22H21BN2O6+H)+: 421.2. MS found: (M+H)+=421.2.

Workup

concentrationThe reaction mixture was concentrated to dryness
additionThe residue was diluted with water
extractionThe aqueous phase was extracted with ethyl acetate
customThe organic phase was separated
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-53ac7ed27f584c1f9e07565cda70d134
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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