1,2-Dichloroethane → HCID 58504456, compound

HRID 2367560Notes

Reaction equation

HRID 2367560 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].[CH2:19]([NH2:26])[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:26][CH2:19][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 7504BenzylamineHCID 181649HOAtHCID 51356009HCID 51356009, compound

Product 1

HCID 58504456HCID 58504456, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2S,5R)-4-{[(1,1-dimethylethyl)oxy]carbonyl}-5-ethyl-2-morpholinecarboxylic acid (0.390 g, 1.504 mmol) in CH2Cl2 (10 mL) were added benzylamine (0.164 mL, 1.504 mmol), HOAt (0.205 g, 1.504 mmol) and EDC (0.346 g, 1.805 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was washed with H2O (3×) and the organics were then dried over Na2SO4 and concentrated to afford the title compound (0.551 g). LC-MS (ES) m/z=249 [M+H-Boc]+.

Workup

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

Sources & evidence

ORD record
ord-2ebf1f1c9bde4752a8961ca534832551
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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