N-(tert-butoxycarbonyl)glycine → HCID 178453815, compound

HRID 1823765Notes

Reaction equation

HRID 1823765 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH:46]1([NH:51][C:52]2[CH:57]=[CH:56][C:55]([S:58]([O:61][C:62]3[CH:71]=[CH:70][C:65]4[NH:66][C:67]([NH2:69])=[N:68][C:64]=4[CH:63]=3)(=[O:60])=[O:59])=[CH:54][CH:53]=2)[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C)C=O>[CH:46]1([NH:51][C:52]2[CH:57]=[CH:56][C:55]([S:58]([O:61][C:62]3[CH:71]=[CH:70][C:65]4[NH:66][C:67]([NH:69][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:68][C:64]=4[CH:63]=3)(=[O:59])=[O:60])=[CH:54][CH:53]=2)[CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508207HCID 178508207, compound

Product 1

HCID 178453815HCID 178453815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

11.3 mg of N-(tert-butoxycarbonyl)glycine, 25 mg HBTU and 12 μl diisopropylethylamine were taken up in 0.4 ml dimethylformamide. Reaction mixture was stirred at room temperature for one hour and 5-(4-cyclopentylaminophenylsulfonyloxy)-1H-benzimidazole-2-ylamine was added in 0.2 ml dimethylformamide. Reaction mixture was then stirred at room temperature for 24 hours. Solvent was evaporated in a Jouan model RC 10.10 centrifuge evaporator and title compound was solubilised in 0.5 ml dimethylsulfoxide for LCMS trigged purification yielding 2.4 mg of N-[5-(4-cyclopentylaminophenylsulfonyloxy)-1H-benzimidazole-2-yl]-tert-butoxycarbonylglycineamid. (LC/MS analysis: retention time=3.87 min., mass spectrum: 530.38, [M+H]+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. stirringwas then stirred at room temperature for 24 hours
  4. customSolvent was evaporated in a Jouan model RC 10.10 centrifuge evaporator and title compound
  5. custompurification

Sources & evidence

ORD record
ord-755e856c6d3e430b881b5d042d155ee2
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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