Acetic Anhydride → HCID 68510668, compound

HRID 1716252Notes

Reaction equation

HRID 1716252 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15][CH2:14]3)=[O:12])[S:8][C:4]=2[CH:3]=1.[CH3:25][C:26](OC(C)=O)=[O:27].CCN(CC)CC>C(Cl)Cl>[N:13]1([C:11](=[O:12])[CH2:10][S:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([NH:1][C:26](=[O:27])[CH3:25])[CH:24]=[CH:23][C:5]=3[N:6]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59467893HCID 59467893, compound

Product 1

HCID 68510668HCID 68510668, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of compound 49 (0.16 g, 0.45 mmol) in dry CH2Cl2 (5 mL) was added Ac2O (0.25 mL, 2.70 mmol) followed by dropwise addition of Et3N (0.25 mL, 1.80 mmol). The reaction was stirred for 2 h under N2. The reaction mixture was diluted with CH2Cl2 (40 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 (EtOAc/hexanes 3:7) to afford 51 as a white solid (154 mg, 86%); MS m/z: 398 (M+H)+. Anal. Calcd. For, C20H19N3O2S2: C, 60.43; H, 4.82; N, 10.57; S, 16.13. Found: C, 60.54; H, 4.91; N, 10.41; S, 15.87.

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 (EtOAc/hexanes 3:7)

Sources & evidence

ORD record
ord-2cf1aded5246432a885a2fa99c138a9a
Source dataset
uspto-grants-2010_09
Patent number
US07803790B2

Reaction notes

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