Ethanol → HCID 11549423, compound

HRID 1158525Notes

Reaction equation

HRID 1158525 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=1)[CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7].[CH2:46]1[O:54][C:53]2[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][C:48]=2[O:47]1.C([O-])([O-])=O.[Na+].[Na+].CCO>COCCOC>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:51]2[CH:50]=[CH:49][C:48]3[O:47][CH2:46][O:54][C:53]=3[CH:52]=2)=[CH:40][CH:39]=1)[CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 11513133HCID 11513133, compound

Product 1

HCID 11549423HCID 11549423, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared according to Method B, using compound 19 (91.9 mg, 0.135 mmol), 3,4-methylenedioxyphenylboronic acid (112 mg, 0.676 mmol), Pd(PPh)3Cl2 (4.70 mg, 0.0067 mmol), 2 M Na2CO3 (aq., 0.203 mL, 0.405 mmol), EtOH (0.4 mL) and DME (1.6 mL). Purification by RP-LC-MS (35 min gradient of 30-100% CH3CN in 0.05% aqueous formic acid) afforded the product (47.7 mg, 49%) as a white solid.

Workup

  1. customPurification by RP-LC-MS (35 min gradient of 30-100% CH3CN in 0.05% aqueous formic acid)

Sources & evidence

ORD record
ord-cfcc9b8e93f6435eb1accd796677d5eb
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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