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tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate

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tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate Basic information

Product Name:
tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate
Synonyms:
  • Tert-Butyl(1R,2S,5S)-2-azido-5-[(diMethylaMino)carbonyl]cyclohexylcarbaMate oxalic acid
  • oxalic acid tert-butyl N-[(1R,2S,5S)-2-aMino-5-(diMethylcarbaMoyl)cyclohexyl]carbaMate
  • (2-Azido-5-diMethylcarbaMoyl-cyclohexyl)-carbaMic acid tert-butyl esteroxalic acid
  • EthanediaMide iMpurity A/Edoxaban Intermediate II
  • tert-butyl ((1R,2S,5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate oxalic acid
  • Edoxaban-1
  • N-[(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]-Carbamic acid, 1,1-dimethylethyl ester, ethanedioate (1:1)
  • 2EthanediaMide iMpurity A
CAS:
1210348-34-7
MF:
C16H29N3O7
MW:
375.42
EINECS:
1592732-453-0
Mol File:
1210348-34-7.mol
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tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate Chemical Properties

storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
color 
White
InChI
InChI=1/C14H27N3O3.C2H2O4/c1-14(2,3)20-13(19)16-11-8-9(6-7-10(11)15)12(18)17(4)5;3-1(4)2(5)6/h9-11H,6-8,15H2,1-5H3,(H,16,19);(H,3,4)(H,5,6)/t9-,10-,11+;/s3
InChIKey
IERZZGXDUZIMSC-FPTARDKGNA-N
SMILES
C(=O)(O)C(=O)O.N([C@H]1[C@H](CC[C@H](C(=O)N(C)C)C1)N)C(=O)OC(C)(C)C |&1:7,8,11,r|
CAS DataBase Reference
1210348-34-7
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tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate Usage And Synthesis

Uses

tert-Butyl [(1R,2S,5S)-2-Amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate Oxalate is a starting material and useful building block of various pharmaceuticals.

Uses

Tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate is also called EthanediaMide iMpurity A. It is a starting material and useful component of various pharmaceuticals. As an organic synthesis intermediate and pharmaceutical intermediate. It could be used in the synthesis and research of the EthanediaMide.

Synthesis

Tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate is prepared by the reaction of benzyl N-[(1S,2R,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-(dimethylcarbamoyl)cyclohexyl]carbamate and Oxalic Acid. The steps are as follows:
Pd-C (230 mg) was added to a solution (35 mL) of benzyl t-butyl{(1S,2R,4S)-4-[(dimethylamino)carbonyl]cyclohexan-1,2-diyl}biscarbamate (2.3 g) in ethanol, and the mixture was stirred in a hydrogen atmosphere for 16 hours. Pd-C was removed by filtration, and the filtrate was concentrated under reduced pressure. Ethyl acetate (20 mL) and anhydrous oxalic acid (493.6 mg) were added to the residue, followed by stirring at room temperature for 17 hours. The formed crystals were recovered by filtration, to thereby yield 1.93 g of the Tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate oxalate.

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