TBAF tetrahydrofuran → HCID 69748745, compound

HRID 1061689Notes

Reaction equation

HRID 1061689 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[C:24]([N:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]([CH2:39][C:40]([NH:42][C@@H:43]([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:44](=[O:54])[CH2:45][O:46][Si](C(C)(C)C)(C)C)=[O:41])[C:29](=[O:62])[C@H:28]1[CH:63]([CH3:65])[CH3:64])(=[O:26])[CH3:25]>O1CCCC1>[C:24]([N:27]1[CH:32]=[C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:30]([CH2:39][C:40]([NH:42][C@@H:43]([CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:44](=[O:54])[CH2:45][OH:46])=[O:41])[C:29](=[O:62])[C@H:28]1[CH:63]([CH3:65])[CH3:64])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69749482HCID 69749482, compound

Product 1

HCID 69748745HCID 69748745, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 M tetrabutylammonium fluoride/tetrahydrofuran solution (0.5 ml) is added to a solution of (3S)-3-{(3R)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-1-tert-butyldimethylsilyloxy-2-oxo-4-phenylbutane (130 mg, Compound No. 7-10) in tetrahydrofuran (0.5 ml), and the mixture is stirred for 2.5 hours. The reaction mixture is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (25.2 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d37d8902b1dd4ea39e68726f536aba36
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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