N-(tert-butoxycarbonyl)glycine → RUC-4

HRID 624679Notes

Reaction equation

HRID 624679 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[S:30][C:11]3=[N:12][C:13]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[CH:14][C:15](=[O:16])[N:10]3[N:9]=2)[CH:5]=[N:6][CH:7]=1.CC(OC([NH:38][CH2:39][C:40](O)=[O:41])=O)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:38][CH2:39][C:40]([NH:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[S:30][C:11]3=[N:12][C:13]([N:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)=[CH:14][C:15](=[O:16])[N:10]3[N:9]=2)[CH:3]=1)=[O:41]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89711500HCID 89711500, compound

Product 1

HCID 71668132RUC-4Yield 110.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-(5-aminopyridin-3-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (20 mg, 0.047 mmol) in DMF (1 ml) is added Boc-gly-OH (16 mg, 0.093 mmol), HATU (35 mg, 0.093 mmol) and Hunig's base (0.024 mmol, 0.14 mmol) and the mixture is stirred at room temperature for 3 h. EtOAc (10 ml) is added and the solution is washed with H2O and brine. The organic layer is dried over Na2SO4. After removing EtOAc in vacuo, the residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/10 gradient) to give the desired product (20 mg, 73%).

Workup

  1. washthe solution is washed with H2O and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customAfter removing EtOAc in vacuo
  4. customthe residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/10 gradient)

Sources & evidence

ORD record
ord-fc95e3153bfd494a9851d6544ac62bbe
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

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