Cyclopentylamine → HCID 68322607, compound

HRID 1521731Notes

Reaction equation

HRID 1521731 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[C:11]([C:15]([OH:17])=O)[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1(N)CCCC1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[N:10]=[C:11]([C:15](=[O:17])[NH:33][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[N:12]([CH3:14])[CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 2906Cyclopentylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27572264-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 68322607HCID 68322607, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-imidazole-2-carboxylic acid (724 mg, 3.0 mmol) in DMF (6 mL) is added TBTU (1.16 g, 3.6 mmol). After 15 min cyclopentylamine (0.44 mL, 4.5 mmol) is added. After 20 h an additional portion of cyclopentylamine (0.44 mL, 4.5 mmol) is added, and stifling continued for a further 24 h. The mixture is diluted with EtOAc and washed in turn with 1M aqueous NaHSO4, Na2CO3 and brine. The organic layer is dried (MgSO4) and evaporated. The crude material is purified by column chromatography using a gradient of 10-100% EtOAc/heptane to afford the title compound (345 mg, 37%).

Workup

  1. washwashed in turn with 1M aqueous NaHSO4, Na2CO3 and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated
  4. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-cea706b253f043e8934d533c34e2b7d5
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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