N,N-Diethylethanamine trihydrofluoride → methyl (1S,4R)-4-hydroxy-4-{5-[3-(hydroxymethyl)-5-nitrophenyl]-1,3-thiazol-2-yl}-2,2-dimethylcyclohexanecarboxylate

HRID 1039948Notes

Reaction equation

HRID 1039948 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:19]2[S:23][C:22]([C@@:24]3([OH:36])[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH3:33])=[O:31])[C:26]([CH3:35])([CH3:34])[CH2:25]3)=[N:21][CH:20]=2)[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C>C(#N)C>[OH:36][C@:24]1([C:22]2[S:23][C:19]([C:12]3[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:10]([CH2:9][OH:8])[CH:11]=3)=[CH:20][N:21]=2)[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH3:33])=[O:31])[C:26]([CH3:35])([CH3:34])[CH2:25]1

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 67432153methyl(1S,4R)-4-{5-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-nitrophenyl]-1,3-thiazol-2-yl}-4-hydroxy-2,2-dimethylcyclohexanecarboxylate

Product 1

HCID 67433080methyl (1S,4R)-4-hydroxy-4-{5-[3-(hydroxymethyl)-5-nitrophenyl]-1,3-thiazol-2-yl}-2,2-dimethylcyclohexanecarboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of Step 3 (4.4 g, 8.23 mmol) in acetonitrile (20 mL) was added triethylamine trihydrofluoride (4 mL, 24.7 mmol). The mixture was stirred for 5 h at room temperature, then quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate (2×), and the combined organics were dried over sodium sulfate, filtered, and concentrated to give methyl(1S,4R)-4-hydroxy-4-{5-[3-(hydroxymethyl)-5-nitrophenyl]-1,3-thiazol-2-yl}-2,2-dimethylcyclohexanecarboxylate (3.5 g, 7.9 mmol, 96% yield) as an orange-maroon oily foam. MS ESI: [M+H]+ m/z 421.1.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionThe mixture was extracted with ethyl acetate (2×)
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f40d7fcbf1b40d9a79668be4efe961a
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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