Acetic Anhydride → HCID 58822110, compound

HRID 2104446Notes

Reaction equation

HRID 2104446 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[NH:21][C:22]([C:24]1[S:25][C:26]3[CH2:27][NH:28][CH2:29][CH2:30][C:31]=3[N:32]=1)=[O:23])=[O:13])=[CH:6]2.C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>CN(C)C=O>[C:40]([N:28]1[CH2:29][CH2:30][C:31]2[N:32]=[C:24]([C:22]([NH:21][C@@H:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:15]3[NH:14][C:12]([C:7]3[NH:8][C:9]4[C:5]([CH:6]=3)=[CH:4][C:3]([Cl:2])=[CH:11][CH:10]=4)=[O:13])=[O:23])[S:25][C:26]=2[CH2:27]1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68451545HCID 68451545, compound

Product 1

HCID 58822110HCID 58822110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (100 mg) obtained in Example 34 was dissolved in N,N-dimethylformamide (3 mL), triethylamine (84 μl) and acetic anhydride (29 μl) were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride and 1N hydrochloric acid were added to the residue for partitioning the mixture. The resultant organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give the title compound (86 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride and 1N hydrochloric acid
  2. additionwere added to the residue
  3. customfor partitioning the mixture
  4. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3)

Sources & evidence

ORD record
ord-7bbeea25028a4f20bbd9ce2ac80fd117
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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