Hydrochloric Acid → 2-(2-bicyclo[2.2.1]heptanylamino)-5,5-bis(2-hydroxyethyl)-1,3-thiazol-4-one

HRID 46128Notes

Reaction equation

HRID 46128 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)([CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)[C:12](=[O:14])[N:13]=1.Cl>C(O)C>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH2:16][OH:17])([CH2:25][CH2:26][OH:27])[C:12](=[O:14])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455195HCID 178455195, compound

Product 1

HCID 1785179402-(2-bicyclo[2.2.1]heptanylamino)-5,5-bis(2-hydroxyethyl)-1,3-thiazol-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bicyclo[2.2.1]heptan-2-ylamino)-5,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)thiazol-4(5H)-one (771 mg, 1.46 mmol) in 15 mL of a 1% HCl solution in ethanol was stirred at room temperature for 3 h. The reaction mixture was then concentrated in vacuo. Flash column chromatography (silica gel, 0-8% MeOH—CH2Cl2) afforded the title compound as a colorless thin film (390 mg). MS (ESI, pos. ion) m/z: 299 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-5dc0ace2ef5c4d928d3416b2dbc2aaa6
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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