1,2-Dichloroethane → HCID 58938767, compound

HRID 387195Notes

Reaction equation

HRID 387195 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](O)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1C(=O)CC[C:25]1=O.C(Cl)CCl.CN>C(Cl)Cl.C1COCC1>[CH:19]1([CH2:18][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]([OH:17])[C:14]([NH:24][CH3:25])=[O:15])[CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 80170N-HydroxysuccinimideHCID 58938951HCID 58938951, compound

Product 1

HCID 58938767HCID 58938767, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(benzyloxycarbonylamino)-4-cyclobutyl-2-hydroxybutanoic acid (250 mg, 0.81 mmol) in DCM (20 mL) was added HOSu (140 mg, 1.22 mmol), EDC (234 mg, 1.22 mmol). After stirring for 1 hour, methylamine in THF (2 N, 0.81 mL) was added to the above mixture. The reaction mixture was stirred for 18 hours and then concentrated in vacuo. The residue was purified by Gilson Prep to afford the title compound (135 mg). 1H-NMR (CDCl3): δ 7.54-7.28 (m, 5H), 6.67 (NH, 1H), 5.03 (dd, 2H), 3.68 (m, 1H), 2.73 (m, 3H), 2.26 (m, 1H), 1.97-1.31 (m, 9H). (M+1) 321.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by Gilson Prep

Sources & evidence

ORD record
ord-fb26b509939e4f8397c3ae8eb0ddfde1
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

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