Acetic Anhydride → HCID 71245377, compound

HRID 1186017Notes

Reaction equation

HRID 1186017 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C:12]1([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16](=[O:26])[NH:17][C@@H:18]([C@H:23]([OH:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:41][C:42](OC(C)=O)=[O:43]>C1COCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C:12]1([C:16](=[O:26])[NH:17][C@@H:18]([C@H:23]([O:25][C:42](=[O:43])[CH3:41])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 71245383HCID 71245383, compound

Product 1

HCID 71245377HCID 71245377, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 4 (3 g, 6.60 mmol) was dissolved in THF (30 mL), Et3N (1.11 mL, 7.92 mmol) and Ac2O (742 mg, 7.26 mmol) were added at RT. The reaction mixture was stirred at RT for 2 h. The volatiles were evaporated under reduced pressure and the residue obtained was diluted with CH2Cl2 and washed with dilute HCl. The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography using 30% EtOAc/Hexane as eluent to yield compound 5 (2.5 g, 76%).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue obtained
  3. washwashed with dilute HCl
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-bf5ebc82e0664112a529b0b23a89ccf5
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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