1,2-Dichloroethane → Benzyl N-(2-aminoethyl)carbamate

HRID 1183814Notes

Reaction equation

HRID 1183814 reaction equation
C(Cl)CCl.C1C=C[C:8]2[N:13](O)N=[N:11][C:9]=2C=1.C(Cl)Cl.[C:18]([O:22][C:23](=O)[C:24]1[CH:29]=[CH:28][C:27](N)=[CH:26][CH:25]=1)(C)(C)C.CN(C=[O:36])C>[Cu](Cl)Cl>[NH2:11][CH2:9][CH2:8][NH:13][C:18](=[O:36])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

Product 1

HCID 2794257Benzyl N-(2-aminoethyl)carbamateYield 92%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

1.5 grams (3.77 mMol) of Fmoc-citruline were dissolved in 3 mL of DMF in a round bottom flask to which was added 0.87 grams (4.5 mMol) of EDC, 0.61 grams (4.5 mMol) of HOBt. 6 mL of DCM were then added followed by the addition 0.88 grams (4.5 mMol) of t-butyl-4-aminobenzoate and a catalytic amount of copper chloride. The reaction mixture was allowed to stir overnight The solvents were evaporated and the crude product purified over silica gel with 5 to 10% MeOH in DCM to give 2 grams of 1 in 92% yield. M+1=574

Workup

  1. customwere evaporated
  2. customthe crude product purified over silica gel with 5 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-597e9ede343c45c588f868c1c89586b9
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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