Morpholine → HCID 10188399, compound

HRID 2187096Notes

Reaction equation

HRID 2187096 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([CH2:33][N:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 69290587HCID 69290587, compound

Product 1

HCID 10188399HCID 10188399, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.38 mmol) 4-chloromethyl-benzoic acid-(3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester in 10 ml CH2Cl2 were added 53 □l (0.38 mmol) Et3N and 33 μl (0.38 mmol) morpholine. After 16 hours the reaction mixture was purified by chromatography over silica gel to give 70 mg (0.12 mmol, 32%) 4-morpholin-4-ylmethyl-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester as a colorless solid.

Workup

  1. customAfter 16 hours the reaction mixture was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-3ebc9e8d59fd4c1092f083cac5474442
Source dataset
uspto-grants-2002_06
Patent number
US06407235B1

Reaction notes

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