1,2-Dichloroethane → HCID 67962335, compound

HRID 1039084Notes

Reaction equation

HRID 1039084 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=C[C:26]2N(O)N=[N:29][C:27]=2[CH:28]=1.CCN(C(C)C)C(C)C.C1(N)CC1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH:27]1([NH:29][C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:14][CH:13]=2)[CH2:28][CH2:26]1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid

Product 1

HCID 67962335HCID 67962335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{4-[(tert-butoxycarbonyl)amino]phenyl}acetic acid (300 mg, 1.2 mmol) was dissolved in DMF (3 ml). EDC (275 mg, 1.4 mmol), HOBt (256 mg, 1.7 mmol), DIEA (450 mg, 3.6 mmol) and cyclopropyl amine (82 mg, 1.4) were added and the mixture stirred at RT for 2 hours. The mixture was diluted into a 10% solution of sodium bicarbonate (aq, 50 ml), extracted with EtOAc (3×30 ml), the organic fractions combined, dried over Na2SO4, filtered and the volatiles removed in vacuum to give the titled compound. LRMS calc: 290.16; obs: 397.27 (M+1).

Workup

  1. extractionextracted with EtOAc (3×30 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-3e9e7f8db0be49c39b80da06b2a0eab2
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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