Tetrabutylammonium Fluoride → HCID 57324460, compound

HRID 1006109Notes

Reaction equation

HRID 1006109 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-4cd760e0e1604798aab76b00e1c06aaa
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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