1,2-Dichloroethane → HCID 58938851, compound

HRID 2425285Notes

Reaction equation

HRID 2425285 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:18][CH:19]1[CH2:22][CH2:21][CH2:20]1)[CH:13]([OH:17])[C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1[C:29](=O)[CH2:28][CH2:27]C1=O.C(Cl)CCl.C1(N)CC1>C(Cl)Cl>[CH:19]1([CH2:18][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]([OH:17])[C:14]([NH:24][CH:29]2[CH2:27][CH2:28]2)=[O:16])[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 80170N-HydroxysuccinimideHCID 58938951HCID 58938951, compound

Product 1

HCID 58938851HCID 58938851, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzyloxycarbonylamino)-4-cyclobutyl-2-hydroxybutanoic acid (600 mg, 1.95 mmol) in DCM (20 mL) was added HOSu (337 mg, 2.93 mmol), EDC (562 mg, 2.93 mmol). After stirring for 1 hour, cyclopropylamine (223 mg, 3.9 mmol) was added to the above mixture. The product was extracted with EtOAc. The combined organic layer was then washed with HCl (1N), water, NaHCO3, and brine and then concentrated in vacuo to afford benzyl 1-cyclobutyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-ylcarbamate (530 mg). (M+1) 347.

Workup

  1. extractionThe product was extracted with EtOAc
  2. washThe combined organic layer was then washed with HCl (1N), water, NaHCO3, and brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-788ada73ce2f4e4f9533141be8908ac5
Source dataset
uspto-grants-2011_06
Patent number
US07964624B1

Reaction notes

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