Morpholine → HCID 86639718, compound

HRID 888677Notes

Reaction equation

HRID 888677 reaction equation
C([O:4][C:5](=[O:76])[CH2:6][C@H:7]([OH:75])[C@H:8]([NH:12][C:13](=[O:74])[C@H:14]([NH:36][C:37](=[O:73])[C@H:38]([NH:43][C:44](=[O:72])[CH2:45][C@@H:46]([OH:71])/[CH:47]=[CH:48]/[CH2:49][CH2:50][S:51][C:52]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:15][S:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([CH3:11])[CH3:10])C=C.N1CCOCC1>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:75][C@H:7]([C@H:8]([NH:12][C:13](=[O:74])[C@H:14]([NH:36][C:37](=[O:73])[C@H:38]([NH:43][C:44](=[O:72])[CH2:45][C@@H:46]([OH:71])/[CH:47]=[CH:48]/[CH2:49][CH2:50][S:51][C:52]([C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH2:39][CH:40]([CH3:41])[CH3:42])[CH2:15][S:16][C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:9]([CH3:11])[CH3:10])[CH2:6][C:5]([OH:76])=[O:4]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86639719HCID 86639719, compound

Product 1

HCID 86639718HCID 86639718, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4C (168 mg, 0.158 mmol) in dry CH3OH (5 mL) at rt was added morpholine (27.6 μl, 0.48 mmol) followed by Pd(PPh3)4 (18.3 mg, 0.016 mmol). After stirring for 2 h the solvent was evaporated, the product rinsed with CH2Cl2 and washed with 1 M HCl (10 mL), sat NaHCO3 (10 mL) and sat. NaCl (10 mL) solutions. The organic layer was then dried with MgSO4 and filtered, the solvent was removed in vacuo and the crude product was washed with hexane (3×20 mL) and purified by flash chromatography (1-20% CH3OH/CHCl3) to give 5C (101 mg, 0.1 mmol, 63%).

Workup

  1. customwas evaporated
  2. washthe product rinsed with CH2Cl2
  3. washwashed with 1 M HCl (10 mL)
  4. dry with materialThe organic layer was then dried with MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. washthe crude product was washed with hexane (3×20 mL)
  8. custompurified by flash chromatography (1-20% CH3OH/CHCl3)

Sources & evidence

ORD record
ord-5ecd08a10e5643cbb04302ee0a362002
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

Loading…