Water → HCID 86615615, compound

HRID 1695099Notes

Reaction equation

HRID 1695099 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])=[CH:16][CH:15]=2)[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:28](O)=O)[N:8]=2)[N:3]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.N[CH2:65][CH2:66][NH:67][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71].O>CN(C=O)C>[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22](=[O:27])[C:23]([F:25])([F:26])[F:24])=[CH:18][CH:19]=2)[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:28][CH2:65][CH2:66][NH:67][C:68]([O:69][C:70]([CH3:71])([CH3:72])[CH3:73])=[O:74])[N:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 187201N-BOC-ethylenediamineHCID 2724699PyBOPHCID 86615616HCID 86615616, compound

Product 1

HCID 86615615HCID 86615615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carboxylic acid 63 (Example 45, 0.10 g, 0.24 mmol) and PyBOP ((Benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate, 0.12 g, 0.24 mmol) are dissolved in 1 mL dry DMF and stirred at room temperature for 30 min. TEA (50 μL) and tert-butyl 2-aminoethylcarbamate (48 mg, 0.3 mmol) are added. The reaction mixture is stirred for additional 3 h and poured into 50 ml of water. The product is extracted with CH2Cl2, dried over MgSO4 and purified via flash column chromatography using CH2Cl2/MeOH (20:1).

Workup

  1. stirringThe reaction mixture is stirred for additional 3 h
  2. extractionThe product is extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. custompurified via flash column chromatography

Sources & evidence

ORD record
ord-3fba020f694f4b4faa1404a127f43804
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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