Acetyl chloride → HCID 86750983, compound

HRID 1684052Notes

Reaction equation

HRID 1684052 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[C:21]([C@H:23]2[CH2:27][S:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[S:24]2)[CH:20]=[C:19]([O:40][CH3:41])[C:4]=1[O:5][CH2:6][CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:10].[C:42](Cl)(=[O:44])[CH3:43].C(N(CC)CC)C>ClCCl>[C:42]([N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:9]([O:8][CH2:7][CH2:6][O:5][C:4]1[C:19]([O:40][CH3:41])=[CH:20][C:21]([C@H:23]2[CH2:27][S:26][C@H:25]([C:28]3[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=3)[S:24]2)=[CH:22][C:3]=1[O:2][CH3:1])=[O:10])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 86750984HCID 86750984, compound

Product 1

HCID 86750983HCID 86750983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trans-2-[{2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)-2,4-dithiolanyl)phenoxy}ethoxycarbonylaminomethyl]pyridine (31) (FIG. 26) (0.313 g,0.520 mmole) was dissolved in 20 ml dry dichloromethane. The reaction was cooled to 0° C. under an argon atmosphere and 44 μl of acetyl chloride was added. The reaction was allowed to warm to room temperature and was stirred overnight. The reaction was recooled to 0° C. and 87 μl triethyl amine and 44 μl acetyl chloride was added. The reaction was then allowed to warm to room temperature and was stirred for an additional 12 hours. The reaction was then quenched with 10% NaHCO3 and extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated to a brown oil which was purified by flash column chromatography using 1:1 hexane/ethyl acetate--1:2 hexane/ethyl acetate as eluent. The column yields 293 mg (88%) as a white foam.

Workup

  1. temperatureto warm to room temperature
  2. customwas recooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringwas stirred for an additional 12 hours
  5. customThe reaction was then quenched with 10% NaHCO3
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated to a brown oil which
  9. customwas purified by flash column chromatography
  10. customThe column yields 293 mg (88%) as a white foam

Sources & evidence

ORD record
ord-70e8b8b477e94a9ba55a3aff0c77e74d
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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