Potassium Hydroxide → 3-[3-{[1-(2-{[(2R)-2-Amino-3-hydroxypropyl]oxy}phenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-4-methylbenzamide

HRID 1697389Notes

Reaction equation

[CH:1]1([NH:4][C:5](=[O:38])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([CH3:36])([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH2:29][C@H:30]4[CH2:34][O:33]C(=O)[NH:31]4)[CH3:21])[C:14]3=[O:37])[CH:7]=2)[CH2:3][CH2:2]1.[OH-].[K+]>O.CO>[NH2:31][C@H:30]([CH2:34][OH:33])[CH2:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:20]([NH:19][C:15]1[C:14](=[O:37])[N:13]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=2[CH3:12])[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:38])[CH:18]=[CH:17][N:16]=1)([CH3:21])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of N-cyclopropyl-4-methyl-3-[3-{[1-methyl-1-(2-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methoxy}phenyl)ethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide (Example 305a) (0.6 g) in water (10 mL) and MeOH (10 mL) was treated with potassium hydroxide (0.130 g) under nitrogen. The resulting mixture was stirred at 50° C. for 16 h. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (250 mL). The organic phase was dried (MgSO4), filtered and evaporated. Purification by preparative HPLC (Phenomenex Gemini column, eluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia) gave the title compound as a solid (0.105 g).

Workup

extractionextracted with ethyl acetate (250 mL)
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
customevaporated
customPurification by preparative HPLC (Phenomenex Gemini column
washeluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia)

Sources & evidence

ORD record: ord-96142845a98a4fe6ba4bce2881d50f30
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163905B2

Reaction notes

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