1,2-Dichloroethane → HCID 58938851, compound

HRID 2092996Notes

Reaction equation

HRID 2092996 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 stiffing 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-98a6bf81598b4bc08a62d0b56cac0872
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

Loading…