1,2-Dichloroethane → HCID 68666149, compound

HRID 1716845Notes

Reaction equation

HRID 1716845 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](Cl)[CH2:11]Cl.[CH:14]1[CH:15]=[CH:16][C:17]2[N:22](O)N=[N:20][C:18]=2[CH:19]=1.[CH3:24]CN(C(C)C)C(C)C.Cl.[CH3:34][O:35][C:36](=[O:41])[C@H:37]([CH2:39][OH:40])[NH2:38]>CN(C=O)C>[CH3:24][N:22]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:19][C:18]=2[N:20]=[C:10]1[CH2:11][C:5]1[CH:4]=[CH:3][C:2]([C:1]([NH:38][C@H:37]([C:36]([O:35][CH3:34])=[O:41])[CH2:39][OH:40])=[O:9])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 68666149HCID 68666149, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of said benzoic acid (0.5 g, 1.87 mmol) in DMF at 0° C., was treated sequentially with EDC (0.47 g, 2.1 mmol, 1.2 eq), HOBt (0.29 g, 2.1 mmol, 1.2 eq), DIPEA (0.8 g, 4.2 mmol, 2.5 eq) and serine methyl ester hydrochloride (0.33 g, 2.1 mmol, 1.2 eq), stirred overnight at room temperature and evaporated under reduced pressure. The resultant residue was partitioned between EtOAc and water. The phases were separated. The organic phase was washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. This residue was purified by column chromatography (silica, CHCl3:MeOH 4%) to afford the title product in 58% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 8.52 (d, J=8 Hz, 1H), 7.95 (s, 1H), 7.84 (d, J=8 Hz, 2H), 7.84 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 2H), 7.14-7.23 (m, 2H), 5.05 (t, J=7.2 Hz, 1H), 4.53 (m, 1H), 4.37 (s, 2H), 3.77 (t, J=7.2 Hz, 1H), 3.70 (s, 3H), 3.64 (s, 3H). LCMS (ESI+) 367 (MH+).

Workup

  1. customevaporated under reduced pressure
  2. customThe resultant residue was partitioned between EtOAc and water
  3. customThe phases were separated
  4. washThe organic phase was washed successively with 1M HCl, water, saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThis residue was purified by column chromatography (silica, CHCl3:MeOH 4%)

Sources & evidence

ORD record
ord-68c71919cb8b4175b65ffe537977dbcf
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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