Triethylamine → 5-Chloropyrazine-2-carboxylic acid 2-benzyloxy-1-benzyloxymethyl-ethyl ester

HRID 719964Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11]([O:18][CH2:19][CH:20](O)[CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([O:18][CH2:19][CH:20]([O:9][C:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10])[CH2:21][O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of 5-chloro-pyrazine-2-carboxylic acid (prepared as in Example 29, 1.00 g, 6.33 mmol) in methylene chloride (30 mL) was treated with 1,3-dibenzyloxy-2-propanol (2.06 g, 7.57 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (1.61 g, 6.34 mmol), and triethylamine (1.83 mL, 12.66 mmol). The mixture was stirred at 25° C. overnight. The solution was extracted with methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with water, a saturated aqueous sodium chloride solution, a 1N aqueous hydrochloric acid solution, and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/1 hexanes/ethyl acetate) afforded the 5-chloropyrazine-2-carboxylic acid 2-benzyloxy-1-benzyloxymethyl-ethyl ester (1.45 g, 55.7%) as a colorless oil.

Workup

extractionThe solution was extracted with methylene chloride
washThe organic layer was washed with water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2eb6ad5dd8434afe8693a089a329da1d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

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