1,2-Dichloroethane → HCID 53248107, compound

HRID 882672Notes

Reaction equation

HRID 882672 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH:9]([S:14]([OH:17])(=[O:16])=[O:15])[CH2:10][C:11]([OH:13])=[O:12].C(Cl)CCl.O[N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29]>CC(N(C)C)=O>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH2:8][CH:9]([S:14]([OH:17])(=[O:15])=[O:16])[CH2:10][C:11]([O:13][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29])=[O:12]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 53248106HCID 53248106, compound

Product 1

HCID 53248107HCID 53248107, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-sulfobutanoic acid (110 mg, 0.418 mmol), EDC (240 mg, 1.25 mmol) and N-hydroxysuccinimide (58 mg, 0.504 mmol) was stirred in 10 ml of DMA for overnight, evaporated and purified on SiO2 chromatography eluted with CH3OH/CH2Cl2/HAc (100:900:1 to 100:600:1) to afford 112 mg (75%) of the title product. 1H NMR (DMF-d7) 6.93 (s, 2H), 4.06 (dd, 1H, J=4.8, 13.1 Hz), 3.80 (dd, 1H, J=10.7, 13.9 Hz), 3.35 (dd, 1H J=3.3, 17.8 Hz), 3.25 (m, 1H), 3.10 (dd, 1H, J=2.2, 16.4 Hz), 2.87 (m, 4H); 13C NMR 172.27, 170.88, 169.29, 135.55, 55.28, 40.22, 32.69, 26.66; ESI MS m/z− 261.70 (M−H).

Workup

  1. customevaporated
  2. custompurified on SiO2 chromatography
  3. washeluted with CH3OH/CH2Cl2/HAc (100:900:1 to 100:600:1)

Sources & evidence

ORD record
ord-115d753448ad4db5a53aa16cc41c1029
Source dataset
uspto-grants-2012_08
Patent number
US08236319B2

Reaction notes

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