1,2-Dichloroethane → HCID 58504507, compound

HRID 2367555Notes

Reaction equation

HRID 2367555 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].[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH:19]1([NH:25][C:16]([C@H:10]2[O:11][CH2:12][C@@H:13]([CH2:14][CH3:15])[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9]2)=[O:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7965CyclohexylamineHCID 181649HOAtHCID 51356009HCID 51356009, compound

Product 1

HCID 58504507HCID 58504507, compoundYield 90.2%

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 cyclohexylamine (0.096 g, 0.964 mmol), HOAt (0.131 g, 0.964 mmol) and EDC (0.222 g, 1.157 mmol), and the reaction was stirred at room temperature overnight. The reaction mixture was washed with H2O (2×) and the organics were dried over Na2SO4 and concentrated to afford the title compound (0.296 g) as a brown oil. LC-MS (ES) m/z=241 [M+H-Boc]+.

Workup

  1. washThe reaction mixture was washed with H2O (2×)
  2. dry with materialthe organics were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5ccd88d43369409ab3f8a069081adb18
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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