Tetrahydrofuran → HCID 178439831, compound

HRID 46150Notes

Reaction equation

HRID 46150 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[S:16][C:17]([CH:22]([CH3:24])[CH3:23])([CH3:21])[C:18](=[O:20])[N:19]=2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>>[OH:8][C@H:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[S:16][C:17]([CH:22]([CH3:24])[CH3:23])([CH3:21])[C:18](=[O:20])[N:19]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 178439832HCID 178439832, compound

Product 1

HCID 178439831HCID 178439831, compound

Procedure

A 5 mL flask was charged flask with 2-((1S,3S)-3-(tert-butyldimethylsilyloxy)cyclopentylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (0.470 g, 1.3 mmol) and tetrabutylammonium fluoride, (1.0M in THF (5.1 ml, 5.1 mmol) and allowed to stir at ambient temp. overnight. The crude reaction mixture was concentrated onto silica gel and the mixture was purified by column chromatography (2-6% MeOH/DCM) to give 2-((1S,3S)-3-hydroxycyclopentylamino)-5-isopropyl-5-methylthiazol-4(5H)-one as a white solid.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated onto silica gel
  3. customthe mixture was purified by column chromatography (2-6% MeOH/DCM)

Sources & evidence

ORD record
ord-ec24b4323dea40f6bee62b9262255346
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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