Acetic Acid → HCID 68512141, compound

HRID 1174419Notes

Reaction equation

HRID 1174419 reaction equation
[CH2:1]([C@H:8]([NH:42][C:43]([C@@H:45]([NH:50][C:51](=[O:54])[O:52][CH3:53])[C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@@H:9]([OH:41])[CH2:10][C@@H:11]([NH:19][C:20](=[O:40])[C@@H:21]([N:26]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=2)[C:27]1=[O:39])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:55][S:56]([CH3:58])=O.C(O)(=O)C.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([C@H:8]([NH:42][C:43](=[O:44])[C@H:45]([C:46]([CH3:47])([CH3:48])[CH3:49])[NH:50][C:51]([O:52][CH3:53])=[O:54])[C@@H:9]([O:41][CH2:55][S:56][CH3:58])[CH2:10][C@@H:11]([NH:19][C:20](=[O:40])[C@@H:21]([N:26]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=2)[C:27]1=[O:39])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 86726258HCID 86726258, compound

Product 1

HCID 68512141HCID 68512141, compoundYield 60%

Procedure

A solution containing the product of Example 10E (1.71 g, 2.3 mmol) in DMSO (3.3 g, 42.3 mmol) was treated with acetic acid (4.1 g, 69 mmol) and acetic anhydride (2.35 g, 23 mmol) at 25° C. for 3 days. Excess ice was added to the mixture which was then made alkaline with 10% sodium carbonate. The mixture was extracted with ethyl acetate, the organic layer was separated, washed with 10% sodium carbonate, water (3×), brine, and dried over sodium sulfate. The solvents were evaporated, and the product was purified by chromatography on silica gel eluting with 30-100% ethyl acetate/dichloromethane to give the title compound (1.1 g, 60% yield).

Workup

  1. additionExcess ice was added to the mixture which
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed with 10% sodium carbonate, water (3×), brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were evaporated
  7. customthe product was purified by chromatography on silica gel eluting with 30-100% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-0d75fd76b18b4cf0a168d059a79d3cb4
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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