Tetrabutylammonium Fluoride → HCID 57324460, compound

HRID 1760797Notes

Reaction equation

HRID 1760797 reaction equation
[CH3:1][O:2][C:3](=[O:45])[C@H:4]([N:11]([S:31]([C:34]1[C:39]([CH3:40])=[CH:38][C:37]([O:41][CH3:42])=[C:36]([CH3:43])[C:35]=1[CH3:44])(=[O:33])=[O:32])[CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18](S(CC[Si](C)(C)C)(=O)=O)[CH:17]=[CH:16]2)[CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:45])[C@H:4]([N:11]([S:31]([C:34]1[C:39]([CH3:40])=[CH:38][C:37]([O:41][CH3:42])=[C:36]([CH3:43])[C:35]=1[CH3:44])(=[O:33])=[O:32])[CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86590024HCID 86590024, compound

Product 1

HCID 57324460HCID 57324460, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 2(R)-{(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-[1-(2-trimethylsilylethanesulfonyl)indol-5-ylmethyl]amino}-3-tert-butoxypropionic acid methyl ester (1.63 g, 2.55 mmol) in tetrahydrofuran (50 mL) was added 1M tetrabutylammonium fluoride (6.4 mL, 6.4 mmol) in tetrahydrofuran, and the mixture heated to 40° C. After 1 h, the reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid. The ethyl acetate layer was separated, dried over magnesium sulfate, and concentrated. The residue was purified by preparative chromatography (20% ethyl acetate-hexanes), to afford 2(R)-{(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-[1H-indol-5-ylmethyl]amino}-3-tert-butoxypropionic acid methyl ester (1 g) which was taken directly into the next reaction.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative chromatography (20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d52b24676131402e9c7f720824101699
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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