Methanol → HCID 22050575, compound

HRID 1867097Notes

Reaction equation

HRID 1867097 reaction equation
[Br:1][C:2]1[C:3](=[O:31])[N:4]([C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[C:22]([O:24]C)=[O:23])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].O1CCCC1.CO.[OH-].[Na+]>O>[Br:1][C:2]1[C:3](=[O:31])[N:4]([C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[C:22]([OH:24])=[O:23])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22050959HCID 22050959, compound

Product 1

HCID 22050575HCID 22050575, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottomed flask was charged with the product of Step 4 (0.77 g, 1.55 mmol), tetrahydrofuran (10 mL), methanol (5 mL), and water (5 mL). To this slurry was added 2.5 N NaOH (1.2 mL, 3.1 mmol). The reaction mixture became clear after 30 minutes and the reaction was complete in 1 h by LC-MS. The organics were removed on the rotary evaporator and the remaining solution was acidified to pH 2-3 with 6N HCl. The desired compound was precipitated by the addition of water and diethyl ether and subsequent filtration. The title compound was isolated as a white powder (0.60 g, 81w). 1H NMR (400 MHz, CD3OD) δ 8.17 (dd, J=2.2 and 8.8 Hz, 1H), 7.82 (d, J=2.2 Hz, 1H), 7.64 (q, 1H), 7.29 (d, J=8.8 Hz, 1H), 7.34 (t, J=8.8 Hz, 2H), 6.60 (s, 1H), 5.34 (s, 2H), 3.87 (s, 3H), 2.01 (s, 3H) ppm. ES-HRMS m/z 480.0259 (M+H calcd for C21H17BrF2NO5 requires 480.0253).

Workup

  1. waitthe reaction was complete in 1 h by LC-MS
  2. customThe organics were removed on the rotary evaporator
  3. customThe desired compound was precipitated by the addition of water and diethyl ether and subsequent filtration

Sources & evidence

ORD record
ord-660205573ca24412bbf821cbb719dc19
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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