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

HRID 1183811Notes

Reaction equation

HRID 1183811 reaction equation
N(C(OC[CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CCCCNC(OC(C)(C)C)=O.C(Cl)CCl.C1C=C[C:42]2[N:47](O)N=[N:45][C:43]=2C=1.CC(N[O:54][C:55](C1C=CC=CC=1)=[O:56])(C)C>C1COCC1.[Cu](Cl)Cl.CN(C=O)C>[NH2:47][CH2:42][CH2:43][NH:45][C:55](=[O:54])[O:56][CH2:22][C:34]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 2724628Fmoc-Lys(Boc)-OHHCID 12439862(Tert-butylamino) benzoate

Product 1

HCID 2794257Benzyl N-(2-aminoethyl)carbamateYield 137.6%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Fmoc-Lys(Boc)-OH (500 mg, 1.07 mmol) in solution of 5% DMF in THF (21 mL) were added EDC (245 mg, 1.28 mmol), HOBt (173 mg, 1.28 mmol) and tert-butyl-4-amino benzoate (247 mg, 1.28 mmol) at room temperature. The mixture thus obtained was stirred for 10 minutes and then copper chloride (172 mg, 1.28 mmol) was added to the mixture. The mixture was stirred overnight. The mixture was concentrated to dryness and then the residue was purified by flash chromatography on silica and eluted with 5% methanol in dichloromethane to give compound 1 as a colorless oil (286 mg, 42%). 1H NMR (CD3OD) δ 1.38 (s, 9H), 1.45-1.54 (m, 4H), 1.58 (s, 9H), 1.80 (m, 2H), 3.05 (t, 2H), 4.22 (m, 2H), 4.38 (d, 2H), 7.30 (m, 2H), 7.38 (m, 2H), 7.68 (m , 4H), 7.78 (d, 2H), 7.90 (d, 2H); LC-MS (ES+), 544 (M+H-Boc)+, 667 (M+Na)+.

Workup

  1. customThe mixture thus obtained
  2. stirringThe mixture was stirred overnight
  3. concentrationThe mixture was concentrated to dryness
  4. customthe residue was purified by flash chromatography on silica
  5. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-dc9168719f5d4721b9a50dc2e4c07c7b
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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