Sodium Hydroxide → 3-Azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyric acid

HRID 1289372Notes

Reaction equation

[N:1]([C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH:5]([O:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1)[C:6]([O:8]C)=[O:7])=[N+:2]=[N-:3].[OH-].[Na+]>CO.C1COCC1>[N:1]([C:4]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:21])[CH:5]([O:10][C:11]1[N:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[N:16]=1)[C:6]([OH:8])=[O:7])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

4.1 g (11 mmol) of methyl 3-azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate (Ex. 2) are dissolved in 100 ml of methanol/THF (1:1) and treated with 13.2 g (33 mmol) of 10% strength sodium hydroxide solution. The mixture is stirred for 6 hours at 50° C. and for 12 hours at room temperature and concentrated on a rotary evaporator. The residue is taken up in 100 ml of water and acidified to pH 2 using 10% strength hydrochloric acid. The resulting precipitate is filtered off with suction, washed with diethyl ether and dried.

Workup

concentrationconcentrated on a rotary evaporator
filtrationThe resulting precipitate is filtered off with suction
washwashed with diethyl ether
customdried

Sources & evidence

ORD record: ord-ff36d2e635804232b850d9274813aa4f
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750469

Reaction notes

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