Acetic Acid → HCID 59223125, compound

HRID 888679Notes

Reaction equation

HRID 888679 reaction equation
C([O:4][C:5](=[O:77])[CH2:6][C@H:7]([OH:76])[C@H:8]([NH:16][C:17](=[O:75])[C@H:18]([NH:40][C:41](=[O:74])[C@H:42]([NH:44][C:45](=[O:73])[CH2:46][C@H:47]([OH:72])/[CH:48]=[CH:49]/[CH2:50][CH2:51][S:52][C:53]([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)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH3:43])[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.CC(O)=O>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:76][C@H:7]([C@H:8]([NH:16][C:17](=[O:75])[C@H:18]([NH:40][C:41](=[O:74])[C@H:42]([NH:44][C:45](=[O:73])[CH2:46][C@H:47]([OH:72])/[CH:48]=[CH:49]/[CH2:50][CH2:51][S:52][C:53]([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)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH3:43])[CH2:19][S:20][C:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([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)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:5]([OH:77])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 59223109HCID 59223109, compound

Product 1

HCID 59223125HCID 59223125, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4D (170 mg, 0.159 mmol), Pd(PPh3)4 (9 mg, 0.008 mmol) in dry methanol (6 mL) under argon was added morpholine (28 μL, 0.32 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 (5-8% MeOH/CH2Cl2 then +0.2% AcOH) to give 5D (130 mg, 0.13 mmol, 61%).

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-346579c75cc14c0593950f26c74c1941
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

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