Tetrabutylammonium Fluoride → HCID 59118110, compound

HRID 896900Notes

Reaction equation

HRID 896900 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:32][C@H:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43]3[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:44]=3)[CH:39]=2)[O:34]1)[CH2:9][C@H:10]([O:24][Si](C(C)(C)C)(C)C)[C:11]1[CH:12]=[N:13][C:14]([N:17]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]2[CH3:23])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:32][C@H:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43]3[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:44]=3)[CH:39]=2)[O:34]1)[CH2:9][C@@H:10]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[C:18]([CH3:23])=[CH:19][CH:20]=[C:21]2[CH3:22])=[CH:15][CH:16]=1)[OH:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59118169Methyl 4-[(2R)-2-[((tert-butoxycarbonyl)[(2R)-2-{[tert-butyl(dimethyl)silyl]-oxy}-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]ethyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoate

Product 1

HCID 59118110HCID 59118110, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-{(2R)-2-[((tert-butoxycarbonyl){(2R)-2-{[tert-butyl(dimethyl)silyl]-oxy}-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]ethyl}-amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoate (Example 371, 213 mg, 0.29 mmol) in THF (5 mL) was added a solution of 1 M tetrabutylammonium fluoride (0.59 mL, 0.59 mmol). The mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. Flash chromatography of the residue over silica gel using 40% ethyl acetate/hexanes afforded 213 mg (92%) of the desired product. The product had: 1H NMR (CDCl3δ): 8.62 (s, 1 H), 8.06 (d, J=8.9 Hz, 2 H), 7.92 (d, J=7.2 Hz, 1 H), 7.58 (d, J=8.8 Hz, 2 H), 7.31-7.40 (m, 2 H), 7.22 (d, J=7.8 Hz, 1 H), 6.89 (d, J=7.9 Hz, 1 H), 5.89 (s, 2 H), 5.10-5.26 (m, 2 H), 4.21-4.50 (m, 1 H), 3.93 (s, 3 H), 3.56-3.88 (m, 4 H), 3.15-3.42 (m, 1 H), 2.78-3.04 (m, 2 H), 2.12 (s, 6 H), 1.65-1.83 (m, 2 H), 1.50 (s, 9 H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3202fab0279046a29fcfb603933cad16
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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