1,2-Dichloroethane → HCID 11514073, compound

HRID 529345Notes

Reaction equation

HRID 529345 reaction equation
CN1CCOCC1.[CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:9].Cl.[NH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH:8]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:16])=[CH:17][CH:18]=1)=[O:9]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 120884-Formylbenzoic acidHCID 122755Glycine methyl ester hydrochlorideHCID 181649HOAt

Product 1

HCID 11514073HCID 11514073, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Added N-methylmorpholine (2.93 mL, 26.6 mmol) to a solution of 4-formylbenzoic acid (1 g, 6.66 mmol), methyl 2-aminoacetate, hydrochloride (1.045 g, 8.33 mmol), 1-hydroxy-7-azabenzotriazole (1.813 g, 13.32 mmol), and EDC (2.55 g, 13.32 mmol) in Dimethyl Sulfoxide (DMSO) (30 mL). Let stir at RT for 16 hours. Added water and extracted with DCM. Combined DCM extracts and washed with water, brine and dried over MgSO4, filtered and rotovapped off DCM. The residue was purified via Biotage (0% to 75% gradient; EtOAc:Hex; 25 g-HP—silica gel column). Obtained 570 mg 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.83 (s, 3H), 4.28 (d, J=5.05 Hz, 2H), 7.98 (s, 4H), 10.10 (s, 1H); [M+H]+=222.1.

Workup

  1. extractionAdded water and extracted with DCM
  2. washCombined DCM extracts and washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe residue was purified via Biotage (0% to 75% gradient; EtOAc:Hex; 25 g-HP—silica gel column)
  6. customObtained 570 mg 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.83 (s, 3H), 4.28 (d, J=5.05 Hz, 2H), 7.98 (s, 4H), 10.10 (s, 1H)

Sources & evidence

ORD record
ord-117c3495c74d4834865a470a6d115298
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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