1,2-Dichloroethane → HCID 59543100, compound

HRID 1876341Notes

Reaction equation

HRID 1876341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[N:22]=1)=[CH:5]2.[C:31](O)(=[O:34])[CH2:32][OH:33].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:32](=[O:33])[CH2:31][OH:34])[CH2:27][CH2:26]3)[N:22]=1)=[CH:5]2

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 59543060HCID 59543060, compound

Product 1

HCID 59543100HCID 59543100, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (23 mg, 0.05 mmol) prepared in Example 117 was dissolved in N,N-dimethylformamide (5 ml). Glycolic acid (15.1 mg, 0.2 mmol), triethylamine (28 ul, 0.2 mmol), EDC (45 mg, 0.23 mmol) and HOBT (40 mg, 0.29 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, 1N hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (5 mg, Yield 19%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-c90a06a41f174a72bac9be1e1e2dbf08
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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