Acetic Anhydride → HCID 59467892, compound

HRID 1404935Notes

Reaction equation

HRID 1404935 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH2:16][CH2:15]1)=[O:13].[CH3:24][C:25](OC(C)=O)=[O:26].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:25]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]([C:12](=[O:13])[CH2:11][S:10][C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH2:15][CH2:16]1)(=[O:26])[CH3:24]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59467890HCID 59467890, compound

Product 1

HCID 59467892HCID 59467892, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of compound 41 (0.41 g, 1.20 mmol) in dry CH2Cl2 (20 mL) were added Ac2O (1.12 mL, 12.0 mmol) followed by dropwise addition of Et3N (1.12 mL, 8.00 mmol), and DMAP (10 mg) The reaction was stirred for 18 h under N2 at room temperature. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with saturated NaHCO3 (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL). Dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the product was purified by column chromatography (CH2Cl2/EtOAc 1:1), and triturated from CH2Cl2/hexanes to afford 48 as a yellow solid (0.24 g, 52%); MS m/z: 384 (M+H)+. Anal. Calcd. For, C19H17N3O2S2.0.1H2O: C, 59.23; H, 4.92; N, 10.91; S, 16.64. Found: C, 58.84; H, 4.55; N, 10.55; S, 16.32.

Workup

  1. washwashed with saturated NaHCO3 (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (CH2Cl2/EtOAc 1:1)
  6. customtriturated from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-ff76b76d38a548bca4a4dfbaf56360a6
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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