Acetic Acid → HCID 59223127, compound

HRID 888675Notes

Reaction equation

HRID 888675 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@H:18]([C:49](=[O:89])[NH:50][C@@H:51]([C:73](=[O:88])[NH:74][C@H:75]([CH:85]([CH3:87])[CH3:86])[C@@H:76]([OH:84])[CH2:77][C:78]([O:80]CC=C)=[O:79])[CH2:52][S:53][C:54]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[NH:19][C:20](=[O:48])[CH2:21][C@H:22]([OH:47])/[CH:23]=[CH:24]/[CH2:25][CH2:26][S:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].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>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@H:18]([C:49](=[O:89])[NH:50][C@@H:51]([C:73](=[O:88])[NH:74][C@H:75]([CH:85]([CH3:86])[CH3:87])[C@@H:76]([OH:84])[CH2:77][C:78]([OH:80])=[O:79])[CH2:52][S:53][C:54]([C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[NH:19][C:20](=[O:48])[CH2:21][C@H:22]([OH:47])/[CH:23]=[CH:24]/[CH2:25][CH2:26][S:27][C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 86639717HCID 86639717, compound

Product 1

HCID 59223127HCID 59223127, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4B (166 mg, 0.13 mmol), Pd(PPh3)4 (15.7 mg, 0.014 mmol) in dry methanol (4 mL) under argon was added morpholine (24 μL, 0.27 mmol) which was allowed to stir for 1 h 20 min. The reaction mixture was concentrated in vacuo, CH2Cl2 (15 mL) was then added before washing with 1M HCl (10 mL), sat. sodium hydrogen carbonate (10 mL) and sat. brine (10 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography on silica gel (eluent 5:95 MeOH/CH2Cl2 then +AcOH 1%) to give a white solid 5B (113 mg, 0.094 mmol, 70%): Rf 0.19 MeOH/CH2Cl2 (5:95); IR (thin film) 3305 (br), 3292 (br), 1731 (s), 1649 (s), 1538 (s).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, CH2Cl2 (15 mL)
  2. additionwas then added
  3. washbefore washing with 1M HCl (10 mL), sat. sodium hydrogen carbonate (10 mL) and sat. brine (10 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography on silica gel (eluent 5:95 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6c1d0f11f14543df87fd314eeda08e58
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

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