HCID 69023069, compound → HCID 44538402, compound

HRID 1968411Notes

Reaction equation

HRID 1968411 reaction equation
C(OC(=O)[N:7]=[C:8]([NH:27]C(OC(C)(C)C)=O)[N:9]([CH3:26])[CH2:10][C:11](=[O:25])[N:12]1[C@H:17]([CH2:18][OH:19])[C@@H:16]([OH:20])[CH:15]([OH:21])[C@H:14]([OH:22])[C@H:13]1[CH2:23][OH:24])(C)(C)C>FC(F)(F)C(O)=O.O>[CH3:26][N:9]([CH2:10][C:11](=[O:25])[N:12]1[C@H:17]([CH2:18][OH:19])[C@@H:16]([OH:20])[CH:15]([OH:21])[C@H:14]([OH:22])[C@H:13]1[CH2:23][OH:24])[C:8]([NH2:27])=[NH:7]

Participants

3

Reactant 1

HCID 69023069HCID 69023069, compound

Product 1

HCID 44538402HCID 44538402, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

In a dry, round bottomed flask, equipped with a magnetic stirrer, 10.12 g (0.020 mol) of tert-butyl(tert-butoxycarbonylamino)(methyl(2-oxo-2-((2R,3R,5R,6R)-3,4,5-trihydroxy-2,6-bis(hydroxymethyl)piperidin-1-yl)ethyl)amino)methylenecarbamate is dissolved in 150 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; 1/5) to yield the creatine homomannojirimycin amide, 1-methyl-1-(2-oxo-2-((2R,3R,5R,6R)-3,4,5-trihydroxy-2,6-bis(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; 1/5)

Sources & evidence

ORD record
ord-94a2c5ec8d6941409f61299d6010b51f
Source dataset
uspto-grants-2013_04
Patent number
US08426395B2

Reaction notes

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