Acetic Acid → HCID 137252530, compound

HRID 538909Notes

Reaction equation

HRID 538909 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:44](=[O:45])[N:14]2[CH:15]([C:38]([O:40]CC=C)=[O:39])[C:16]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:36][C:35](=[O:37])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(CCCC)C([O-])=O)C.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(O)=O>C(Cl)Cl.C(OCC)(=O)C.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>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:44](=[O:45])[N:14]2[CH:15]([C:38]([OH:40])=[O:39])[C:16]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:36][C:35](=[O:37])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 137252531HCID 137252531, compound

Product 1

HCID 137252530HCID 137252530, compoundYield 135%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 9 and 10 (0.071 g, 0.114 mmol) were dissolved in 5 mL of dry methylene chloride. Sodium 2-ethylhexanoate (0.019 g, 0.11 mmol) was dissolved in 2 mL of ethyl acetate. After these two solutions were mixed together, PPh3 (0.01 g, 0.04 mmol) and Pd(PPh3)4 (0.01 g, 0.009 mmol) were added. The combined reaction mixture was stirred for 1.5 h at rt. AcOH (0.5 mL) was added to the solution and the reaction mixture was evaporated in vacuo. The residue was re-evaporated from toluene to yield two separable isomers, 23 and 24 (0.09 g). The crude product was used for the next step without any purification.

Workup

  1. additionAfter these two solutions were mixed together
  2. customThe combined reaction mixture
  3. customthe reaction mixture was evaporated in vacuo
  4. customThe residue was re-evaporated from toluene

Sources & evidence

ORD record
ord-3f0ed95913734917a83de140f1565cdf
Source dataset
uspto-grants-2014_10
Patent number
US08865891B2

Reaction notes

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