1,2-Dichloroethane → HCID 57945508, compound

HRID 882682Notes

Reaction equation

HRID 882682 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]([CH2:7][CH2:8][S:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:4]([OH:6])=[O:5].O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25].C(Cl)CCl>CC(N(C)C)=O>[CH3:17][N:2]([CH3:1])[CH:3]([CH2:7][CH2:8][S:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:4]([O:6][N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25])=[O:5]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 57945497HCID 57945497, compound

Product 1

HCID 57945508HCID 57945508, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-(dimethylamino)-4-(pyridin-2-yldisulfanyl)butanoic acid (218) (92 mg, 0.338 mmol), 1-hydroxypyrrolidine-2,5-dione (65 mg, 0.565 mmol) and EDC (185 mg, 0.965 mmol) was stirred in 3 ml of DMA at 50° C. overnight. The mixture was evaporated and purified on a SiO2 column eluted with from 1:10 to 1:4 of methanol/CH2Cl2 to afford 43 mg (35%) of the title product. 1H NMR (CDl3OD) 8.40 (m, 1H), 7.83 (m, 2H), 7.22 (m, 1H), 3.34 (m, 1H), 2.82 (m, 2H), 2.75 (s, 4H), 2.66 (s, 6H), 1.98 (m, 2H); 13C NMR 177.21, 161.78, 161.12, 150.68, 139.37, 122.70, 121.66, 70.80, 44.16, 43.15, 36.06, 27.38; ESI MS m/z+369.2 (M+H).

Workup

  1. customThe mixture was evaporated
  2. custompurified on a SiO2 column
  3. washeluted with from 1:10 to 1:4 of methanol/CH2Cl2

Sources & evidence

ORD record
ord-e8c5bc4adebc47e18c340d2d2f8a70da
Source dataset
uspto-grants-2012_08
Patent number
US08236319B2

Reaction notes

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