1,2-Dichloroethane → HCID 67607018, compound

HRID 1965217Notes

Reaction equation

HRID 1965217 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[NH:25][CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:40](O)(=[O:44])[C:41]([CH3:43])=[O:42].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:40](=[O:44])[C:41](=[O:42])[CH3:43])[CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1060Pyruvic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67606764HCID 67606764, compound

Product 1

HCID 67607018HCID 67607018, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of amine 84 (480 mg, 0.87 mmol) in DCM (8 mL) was cooled to 0° C. and treated with pyruvic acid (0.06 mL, 0.91 mmol), EDC (200 mg, 1.04 mmol), HOBt (141 mg, 1.04 mmol), and DIPEA (0.47 mL, 2.69 mmol). The reaction mixture was allowed to warm to ambient temperature. After 16 h, the reaction mixture was diluted with DCM, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 87 (529 mg, 97%) as a white foam that was used with out further purification. 1H NMR (CDCl3, 300 MHz): δ7.10-7.01 (m, 1H), 6.88 (br s, 1H), 6.71-6.64 (m, 1H), 6.56-6.53 (m, 1H), 4.72-4.68 (m, 1H), 4.62-4.53 (m, 2H), 4.44 (d, J=6.3 Hz, 1H), 4.15-3.97 (m, 2H), 3.89-3.81 (m, 1H), 3.72-3.61 (m, 1H), 3.53-3.36 (m, 1H), 2.88-2.79 (m, 4H), 2.49-2.00 (m, 5H), 1.49 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.98 (s, 9H) ppm.

Workup

  1. washwashed successively with 1M HCl, saturated aqueous NaHCO3, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77574b78370b479a89fa48b360418c15
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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