Tetrabutylammonium Fluoride → 3-{2-[2-(2-hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814338Notes

Reaction equation

HRID 1814338 reaction equation
[C:1]([O:5][C:6](=[O:49])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[O:38][Si](C(C)C)(C(C)C)C(C)C)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[NH4+].[Cl-]>[C:1]([O:5][C:6](=[O:49])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[OH:38])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86588230N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester

Product 1

HCID 865882313-{2-[2-(2-hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

N-Methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester (270 mg, 0.38 mmol) was stirred with TBAF (0.45 mL of 1.0 M soln in THF, 0.45 mmol) in freshly distilled THF (1.45 mL) at 0° C. for fifteen minutes and then at room temperature for 1.5 h. The reaction mix was diluted with saturated aq. NH4Cl and was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 50% EtOAc-hexanes) to give 3-{2-[2-(2-hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester in quantitative yield. MS (APCI) m/z 557.3 (M−1).

Workup

  1. additionThe reaction mix
  2. extractionwas extracted three times with EtOAc
  3. washwashed with brine solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (SiO2, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4c8a7183f1924503954a4c34f095f419
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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