4-Methylmorpholine → N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester

HRID 1070439Notes

Reaction equation

HRID 1070439 reaction equation
[NH2:1][C:2]1([C:9]([O-:11])=[O:10])[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][CH2:5]2.[C:12]1([S:18]([N:21]2[CH2:28][CH2:27][CH2:26][C@H:22]2[C:23](O)=[O:24])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[CH3:30]N(C)CCCN=C=NCC.CN1CCOCC1>O1CCCC1>[C:12]1([S:18]([N:21]2[CH2:28][CH2:27][CH2:26][C@H:22]2[C:23]([C:3]23[CH2:8][CH:6]([CH2:5][CH2:4]2)[CH2:7][C:2]3([NH2:1])[C:9]([O:11][CH3:30])=[O:10])=[O:24])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 720844(2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86759759HCID 86759759, compound

Product 1

HCID 86759758N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-2-norbornanecarboxylate, methyl ester hydrochloride (400 mg, 2.0 mmol), N-benzenesulfonyl-(L)-proline (510 mg, 2.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (306 mg, 2.0 mmol), 1-hydroxbenzotriazole (202 mg, 2.0 mmol) in 4 mL of tetrahydrofuran at 0° C. was added N-methyl morpholine (0.22 mL, 2.0 mmol). After 15 min at 0° C., the reaction mixture was stirred at room temperature for 16 h, and was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with 10:1 methylene chloride/ethyl acetate to give the title compound (478 mg, 59%) as a mixture of diastereomers.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluted with 10:1 methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-6921d2ce58384a119f112e8892218a20
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

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