Tetrabutylammonium Fluoride → HCID 60083609, compound

HRID 1883160Notes

Reaction equation

HRID 1883160 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].CC(O[Si](C(C)C)(C(C)C)C(C)C)(C)CN1C2C(=CC=CC=2)C=C1C(O)=O.[C:46]([CH:48]([NH:53][C:54]([CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH:57]1[NH:62][C:63]([C:65]1[N:66]([CH2:74][C:75]([OH:78])([CH3:77])[CH3:76])[C:67]2[C:72]([CH:73]=1)=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])=[O:55])[CH2:49][CH:50]([CH3:52])[CH3:51])#[N:47]>C1COCC1>[C:46]([C@@H:48]([NH:53][C:54]([C@@H:56]1[CH2:61][CH2:60][CH2:59][CH2:58][C@@H:57]1[NH:62][C:63]([C:65]1[N:66]([CH2:74][C:75]([OH:78])([CH3:76])[CH3:77])[C:67]2[C:72]([CH:73]=1)=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])=[O:55])[CH2:49][CH:50]([CH3:52])[CH3:51])#[N:47]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 20740360HCID 20740360, compoundHCID 23510136HCID 23510136, compound

Product 1

HCID 60083609HCID 60083609, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Proceeding as described in Example 11, followed by treatment with 1M TBAF in THF at 50° C. for 12 h, 1-(2-Methyl-2-triisopropylsilanyloxy-propyl)-1H-indole-2-carboxylic acid (100 mg, 0.25 mmol) was concerted to 1-(2-hydroxy-2-methyl-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide (80 mg; SiO2 PTLC: 50% ethyl acetate/hexanes; mp: 101.5-105.5° C.; MS: M+H=453).

Sources & evidence

ORD record
ord-6f0781dd6ac0474f9a04495f6d27ac92
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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