3-Fluorobenzylic alcohol → HCID 69523283, compound

HRID 348447Notes

Reaction equation

HRID 348447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17][CH2:18][C:19]([OH:21])=[O:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.[F:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=1)[CH2:55]O>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[F:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=1)[CH2:55][O:20][C:19](=[O:21])[CH2:18][S:17][C:14]1[N:15]=[CH:16][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:12][N:13]=1

Participants

8

Reactant 4

HCID 680083-Fluorobenzylic alcoholHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 21087357HCID 21087357, compound

Product 1

HCID 69523283HCID 69523283, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid (40 mg, 0.13 mmol) in THF (1 mL) was added diisopropylethylamine (45 μL, 0.26 mmol) and TSTU (55 mg, 0.18 mmol). After stirring for 5 min, 3-fluorobenzyl alcohol (18 μL, 0.17 mmol) and DMAP (18 mg, 0.15 mmol) were added and the solution was stirred for 18 h. Ethyl acetate was added, and the reaction was quenched with 3% HCl. The layers were separated, and the organic layer was washed successively with 5% NaHCO3, water, and brine. The brown organic layer was passed through a plug of SiO2 and washed with 50% ethyl acetate/hexane. The filtrate was concentrated to afford a yellow solid. Flash chromatography through SiO2 using 25% ethyl acetate/hexane afforded 15.0 mg (28% yield) of the titled product as a white solid. ESI-MS m/z 416 (MH+), 414 (M−H)−.

Workup

  1. stirringthe solution was stirred for 18 h
  2. customthe reaction was quenched with 3% HCl
  3. customThe layers were separated
  4. washthe organic layer was washed successively with 5% NaHCO3, water, and brine
  5. washwashed with 50% ethyl acetate/hexane
  6. concentrationThe filtrate was concentrated
  7. customto afford a yellow solid

Sources & evidence

ORD record
ord-6b9fb09124414ad484fda0a4148daf13
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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