Morpholine → HCID 68619808, compound

HRID 1433774Notes

Reaction equation

HRID 1433774 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13]OS(C)(=O)=O)=[CH:7][CH:6]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(O)C>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86614671HCID 86614671, compound

Product 1

HCID 68619808HCID 68619808, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (R)-tert-butoxycarbonylamino-[4-(2-methanesulfonyloxy-ethoxy)-phenyl]-acetic acid methyl ester (50 mg, 0.12 mmol) in ethanol (1 mL) was added morpholine (0.043 mL, 0.49 mmol) at room temperature. The reaction mixture was refluxed for 1 hour. The solvent was evaporated and the crude product was purified by chromatography over silica gel eluted with 1:1 v/v hexanes/ethyl acetate to give (R)-tert-butoxycarbonylamino-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetic acid methyl ester (45 mg, 92% yield) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe solvent was evaporated
  3. customthe crude product was purified by chromatography over silica gel
  4. washeluted with 1:1 v/v hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6ba739fdfbe44a91b9b289c06807b607
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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