1,2-Dichloroethane → (3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide

HRID 1366410Notes

Reaction equation

HRID 1366410 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([OH:17])=O)[CH2:5][O:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(Cl)CCl>C(Cl)Cl>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:6]([C:15]([NH:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:17])[CH2:5][O:4][CH2:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

Product 1

HCID 59452664(3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamideYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (69.67 g, 296.2 mmol) and 1-hydroxybenzotriazole (48.01 g, 355.4 mmol) in DCM (990 mL) was cooled to 0° C. To the mixture was added 4-methylmorpholine (163 mL, 1483 mmol), benzyl amine (35.6 mL, 325.9 mmol), and EDC (62.46 g, 325.8 mmol). The yellow solution was stirred overnight at room temperature, and was then washed with water (500 mL), 6 N aqueous HCl (300 mL), and water (200 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude (3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide (97.05 g, >100% crude yield) as a yellow foam. LCMS: (M+H)+: 325.2.

Workup

  1. washwas then washed with water (500 mL), 6 N aqueous HCl (300 mL), and water (200 mL)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74197559e0454736b72b60b8f09ad410
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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