HCID 69026682, compound → HCID 44538400, compound

HRID 1968410Notes

Reaction equation

HRID 1968410 reaction equation
C(OC(=O)[N:7]=[C:8]([NH:25]C(OC(C)(C)C)=O)[N:9]([CH3:24])[CH2:10][C:11](=[O:23])[N:12]1[CH2:17][C@H:16]([OH:18])[C@@H:15]([OH:19])[C@@H:14]([OH:20])[CH:13]1[CH2:21][OH:22])(C)(C)C>FC(F)(F)C(O)=O.O>[CH3:24][N:9]([CH2:10][C:11](=[O:23])[N:12]1[CH2:17][C@H:16]([OH:18])[C@@H:15]([OH:19])[C@@H:14]([OH:20])[CH:13]1[CH2:21][OH:22])[C:8]([NH2:25])=[NH:7]

Participants

3

Reactant 1

HCID 69026682HCID 69026682, compound

Product 1

HCID 44538400HCID 44538400, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

In a dry, round bottomed flask, equipped with a magnetic stirrer, 23.81 g (0.050 mol) of tert-butyl(tert-butoxycarbonylamino)(methyl(2-oxo-2-((3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)ethyl)amino)methylenecarbamate is dissolved in 275 mL of a trifluoroacetic acid:H2O (1:1) mixture. The resultant mixture is stirred for 2 hours at room temperature, after which it is concentrated under reduced pressure and then purified by flash chromatography (ethyl acetate/hexanes; 2/3) to yield the creatine deoxygalactonojirimycin amide, 1-methyl-1-(2-oxo-2-((3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)ethyl)guanidine.

Workup

  1. customIn a dry, round bottomed flask, equipped with a magnetic stirrer
  2. concentrationafter which it is concentrated under reduced pressure
  3. custompurified by flash chromatography (ethyl acetate/hexanes; 2/3)

Sources & evidence

ORD record
ord-093f81f22e394a16b0dd1224a489d00f
Source dataset
uspto-grants-2013_04
Patent number
US08426395B2

Reaction notes

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