1,2-Dichloroethane → HCID 51354039, compound

HRID 2367552Notes

Reaction equation

HRID 2367552 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][CH3:15])[CH2:12][O:11][C@H:10]([C:16]([OH:18])=O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@@H:10]([C:16]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])[O:11][CH2:12]1)[CH3:15]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 181649HOAtHCID 51356009HCID 51356009, compound

Product 1

HCID 51354039HCID 51354039, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2S,5R)-4-{[(1,1-dimethylethyl)oxy]carbonyl}-5-ethyl-2-morpholinecarboxylic acid (0.250 g, 0.964 mmol) in CH2Cl2 (10 mL) were added aniline (0.088 mL, 0.964 mmol), HOAt (0.131 g, 0.964 mmol) and EDC (0.222 g, 1.157 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water (2×), and the organics were dried over Na2SO4 and concentrated to afford the title compound (0.247 g) as a brown oil. LC-MS (ES) m/z=240 [M+H]+.

Workup

  1. washThe reaction mixture was washed with water (2×)
  2. dry with materialthe organics were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-53738a7a311f4cc29a4f1c12d9588519
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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