Acetic Anhydride → HCID 178499576, compound

HRID 970147Notes

Reaction equation

HRID 970147 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([OH:17])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[N:27][C:28]#[N:29])[C:6]=2[CH:30]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].C(N([CH2:43][CH3:44])CC)C.C([O-])(O)=[O:46].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([O:17][C:43](=[O:46])[CH3:44])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[N:27][C:28]#[N:29])[C:6]=2[CH:30]=1)[C:31]([CH3:32])=[O:33]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178499572HCID 178499572, compound

Product 1

HCID 178499576HCID 178499576, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

88 mg (0.21 mmol) of the compound obtained in example 5 was dissolved in methylenechloride, then 61 μl (0.64 mmol) of acetic anhydride, 120 μl (0.86 mmol) of triethylamine and 8 mg (0.06 mmol) of 4-dimethylaminopyridine were added thereto. The reaction was stirred at room temperature for 12 hours, saturated NaHCO3 solution was added, aqueous layer was extracted with methylenechloride. Organic layer was washed with brine and dried over anhydrous MgSO4, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2), to give 35 mg (yield: 34%) of the target compound.

Workup

  1. extractionaqueous layer was extracted with methylenechloride
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-6cc16b3d919c4c03b3990da95e342fee
Source dataset
uspto-grants-2007_12
Patent number
US07309793B2

Reaction notes

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