Sodium Hydroxide → HCID 59063643, compound

HRID 49405Notes

Reaction equation

[OH:1][C@H:2]([C:20]1[CH:21]=[CH:22][C:23]([NH:26]C(=O)C)=[N:24][CH:25]=1)[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C.O>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C@@H:2]([OH:1])[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([CH3:19])[S:17][CH:18]=3)=[CH:10][CH:9]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a round-bottomed flask, (R)-N-[5-(1-hydroxy-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamino}-ethyl)-pyridin-2-yl]-acetamide (74 mg, 0.18 mmol) was dissolved in 1.0 mL of ethanol, and 1.0 mL of 2 M sodium hydroxide was added to the solution. The reaction mixture was then heated to about 80° C. for about twenty minutes, and was then diluted with water and adjusted to about pH 11. The aqueous phase was extracted with four portions of methylene chloride, and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride) to afford 49 mg (74%) of the desired product. LRMS ([M+1]+): 371.2.

Workup

extractionThe aqueous phase was extracted with four portions of methylene chloride
dry with materialthe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride)

Sources & evidence

ORD record: ord-cd42b43cdae6467d874d080c1d60e5ef
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706743B2

Reaction notes

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