1,2-Dichloroethane → HCID 58938809, compound

HRID 387198Notes

Reaction equation

HRID 387198 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:18][CH:19]1[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:23]1C(=O)CC[C:24]1=O.C(Cl)CCl.CN>C(Cl)Cl.C1COCC1>[CH:19]1([CH2:18][C@H: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:23][CH3:24])=[O:15])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 80170N-HydroxysuccinimideHCID 58938722HCID 58938722, compound

Product 1

HCID 58938809HCID 58938809, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-3-(benzyloxycarbonylamino)-4-cyclopropyl-2-hydroxybutanoic acid (180 mg, 0.26 mmol) in DCM (20 mL) was added HOSu (105 mg, 0.92 mmol), EDC (175 mg, 0.92 mmol). After stirred for 30 minutes, methylamine in THF (2 N, 0.92 mL) was added to above mixture. The reaction mixture was stirred for 18 hours and then concentrated in vacuo. The residue was purified by Gilson Prep to afford title compound (50 mg). 1H-NMR (CDCl3): δ 7.53-7.26 (m, 5H), 6.83 (NH, 1H), 5.25 (NH, 1H), 5.05 (m, 2H), 4.25-3.89 (m, 3H), 2.70 (m, 3H), 1.4 (m, 1H), 0.86 (m, 1H), 0.61 (m, 1H), 0.38 (m, 2H), 0.33 (m, 2H). (M+1) 307.

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-f8b0dde2b42d405c959c58dfdf34d072
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

Loading…