Triethylamine → HCID 58504652, compound

HRID 2367341

Reaction equation

HRID 2367341 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[OH:30].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[OH:30][C@@H:25]1[CH2:26][CH2:27][CH2:28][CH2:29][C@H:24]1[NH:23][C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)=[O:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27763534-Benzylmorpholine-2-carboxylic acid

Product 1

HCID 58504652HCID 58504652, compoundYield 73.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(phenylmethyl)-2-morpholinecarboxylic acid (5 g, 22.60 mmol) and DMF (0.1 mL) in CH2Cl2 (113 mL) was added oxalyl chloride (2.97 mL, 33.9 mmol) at 25° C. The mixture was stirred at this temperature for 1 hour and the mixture turned clear. The solvent and excess of oxalyl chloride were removed in vacuo, and the resulting residue was dissolved in CH2Cl2 (113 mL). (1R,2R)-2-Aminocyclohexanol (2.60 g, 22.60 mmol) and triethylamine (12.60 mL, 90 mmol) were added, and the resulting mixture was stirred overnight. Water (80 mL) was added to quench the reaction. the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×80 mL). The combined organics were washed with sat. NaHCO3(aq) (80 mL), then brine (2×80 mL), dried (MgSO4), and evaporated to afford the title compound (5.3 g). LC-MS (ES) m/z=319 [M+H]+.

Workup

  1. customThe solvent and excess of oxalyl chloride were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (113 mL)
  3. stirringthe resulting mixture was stirred overnight
  4. customto quench
  5. customthe reaction
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×80 mL)
  8. washThe combined organics were washed with sat. NaHCO3(aq) (80 mL)
  9. dry with materialbrine (2×80 mL), dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-90fe2358a9b748329b0dcc83ddab5694
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Linked notes

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