1,2-Dichloroethane → HCID 58938767, compound

HRID 2092995Notes

Reaction equation

HRID 2092995 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 stiffing 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. concentrationconcentrated in vacuo
  2. customThe residue was purified by Gilson Prep

Sources & evidence

ORD record
ord-c8f5392906a443bda14f22cbc85e9bf5
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

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