Morpholine → HCID 59223120, compound

HRID 888681Notes

Reaction equation

HRID 888681 reaction equation
C([O:4][C:5](=[O:83])[CH2:6][C@H:7]([OH:82])[C@H:8]([NH:16][C:17](=[O:81])[C@H:18]([NH:40][C:41](=[O:80])[C@H:42]([NH:50][C:51](=[O:79])[CH2:52][C@H:53]([OH:78])/[CH:54]=[CH:55]/[CH2:56][CH2:57][S:58][C:59]([C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:19][S:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C=C.N1CCOCC1>CO.C(Cl)Cl.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:82][C@H:7]([C@H:8]([NH:16][C:17](=[O:81])[C@H:18]([NH:40][C:41](=[O:80])[C@H:42]([NH:50][C:51](=[O:79])[CH2:52][C@H:53]([OH:78])/[CH:54]=[CH:55]/[CH2:56][CH2:57][S:58][C:59]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:19][S:20][C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:5]([OH:83])=[O:4]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 59223116HCID 59223116, compound

Product 1

HCID 59223120HCID 59223120, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4E (210 mg, 0.184 mmol), Pd(PPh3)4 (21 mg, 0.018 mmol) in dry methanol/CH2Cl2 (5:1, 6 mL) under argon was added morpholine (32 μL, 0.37 mmol) which was allowed to stir for 3 h. The reaction mixture was concentrated in vacuo, CH2Cl2 (20 mL) was then added before washing with 1M HCl (15 mL), sat. sodium hydrogen carbonate (15 mL), sat. brine (15 mL), dried over MgSO4 and concentrated in vacuo. Purification was then carried out by column chromatography on silica gel (6-10% MeOH/CH2Cl2) to give 5E (140 mg, 0.13 mmol, 69%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, CH2Cl2 (20 mL)
  2. additionwas then added
  3. washbefore washing with 1M HCl (15 mL), sat. sodium hydrogen carbonate (15 mL), sat. brine (15 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-069bc3ef77574fb3b67945a2a4981f0b
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

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