Tetrahydrofuran → HCID 67021661, compound

HRID 244264Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[C:69]3[N:68]=[CH:67][N:66]=[C:57]([NH:58][CH2:59][C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[C:56]=3[N:55]=[CH:54]1)[O:30]2)[CH2:32][O:33][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O:70]1CCCC1>>[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[C:69]3[N:68]=[CH:67][N:66]=[C:57]([NH:58][C:59](=[O:70])[C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[C:56]=3[N:55]=[CH:54]1)[O:30]2)[CH2:32][OH:33])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 67132300HCID 67132300, compound

Product 1

HCID 67021661HCID 67021661, compound

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 1.0 ml, 1.0 mmol) was added, at room temperature, to a tetrahydrofuran solution (7.0 ml) of Compound 42 (173.6 mg, 0.244 mmol), and the mixture was stirred for 25 minutes at room temperature. The reaction mixture was distilled under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (CHCl3-MeOH, 15:1) to obtain a white powder, Compound 43 (115.4 mg, 0.244 mmol, quant.).

Workup

distillationThe reaction mixture was distilled under reduced pressure
customthe resulting crude product was purified by silica gel column chromatography (CHCl3-MeOH, 15:1)

Sources & evidence

ORD record: ord-05590abf772948d3a86207cbb6204572
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE044779E1

Reaction notes

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