Morpholine → HCID 66918676, compound

HRID 1367453Notes

Reaction equation

HRID 1367453 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12]([OH:14])=O)=[O:5])[CH3:2].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59619308HCID 59619308, compound

Product 1

HCID 66918676HCID 66918676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (1R,2R)-4-oxo-cyclopentane-1,2-dicarboxylic acid monoethyl ester (10.0 mmol) in tetrahydrofuran (25 ml) was subsequently added morpholine (11 mmol) triethylamine (70 mmol), 1-hydroxybenzotriazole hydrate (20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 20 mmol) and stirring was continued at 22° C. for 4 h. The mixture was partitioned between ethyl acetate and 1N aqueous HCl, the organic layer was washed with saturated aqueous Na2CO3, dried and evaporated to give the title compound as pale brown oil. MS: 270.3 (M+H)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1N aqueous HCl
  2. washthe organic layer was washed with saturated aqueous Na2CO3
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-13365a3f254741d79502adf93aaf14ff
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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