Tetrabutylammonium Fluoride → HCID 57324460, compound

HRID 2297990Notes

Reaction equation

HRID 2297990 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-75b0fc2bfb9e4e3f9ac415e3ff1e32cd
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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