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

HRID 1366557Notes

Reaction equation

HRID 1366557 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.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN1CCOCC1.ON1C2N=CC=CC=2N=N1.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:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH2:5][O:4][CH2:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

Product 1

HCID 18346148(3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamideYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (4.611 g, 19.60 mmol) in DCM (65 mL) was added benzylamine (2.6 mL, 23.80 mmol), N-methylmorpholine (11 mL, 100.0 mmol), 1-hydroxy-7-azabenzotriazole (3.20 g, 23.51 mmol), and EDC (4.51 g, 23.53 mmol). The solution was stirred overnight and then diluted with DCM (100 mL). The solution was washed with 6 N aq. HCl (2×100 mL), and the organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide crude (3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide (6.454 g, >100% crude yield) as a pale yellow foam. LCMS: (M+H)+: 325.2.

Workup

  1. washThe solution was washed with 6 N aq. HCl (2×100 mL)
  2. dry with materialthe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43f2d0f67f1f433cab384db1b28a2fcb
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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