1,2-Dichloroethane → HCID 58938809, compound

HRID 2092998Notes

Reaction equation

HRID 2092998 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-e6f1695efdb54c4ba364733dbddc4ebd
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

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