Acetic Acid → HCID 57589818, compound

HRID 1783419Notes

Reaction equation

HRID 1783419 reaction equation
[Si]([N:8]1[C:11](=[O:12])[C@H:10]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]=2)[C@H:9]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])(C(C)(C)C)(C)C.[F-].[NH4+].C(O)(=O)C>CO.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:24]([O:23][C:21]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:16]1[CH:15]=[C:14]([CH2:13][C@H:10]2[C:11](=[O:12])[NH:8][C@@H:9]2[C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])[CH:19]=[CH:18][N:17]=1)=[O:22])([CH3:26])([CH3:27])[CH3:25]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 25516Ammonium fluorideHCID 57589856HCID 57589856, compound

Product 1

HCID 57589818HCID 57589818, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Ester 18 (127 mg, 0.20 mmol) was dissolved in 1 mL dry methanol at room temperature. 1 mL of a 0.5 M solution of ammonium fluoride in methanol (0.5 mmol, 2.5 equiv.) was added, then 60 mg acetic acid (1 mmol, 5 equiv). The reaction was stirred overnight under argon, diluted with 20 mL ethyl acetate and 20 mL saturated sodium bicarbonate solution. The water layer was washed with 3 portions of ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography eluting with 3:1 methylene chloride/ethyl acetate to yield 19 (72 mg, 69%). MS: 611.2 [M+H]+.

Workup

  1. washThe water layer was washed with 3 portions of ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with 3:1 methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-de8ad8713eec4f30805385a65bb90772
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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