1-Butanol → HCID 136381449, compound

HRID 2191022Notes

Reaction equation

HRID 2191022 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)[O:10][CH:11](C2C=CC=CC=2)[CH:12]2[CH:16]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]([O:26][CH3:27])[CH:14]([N:28]3[CH:36]=[N:35][C:34]4[C:33](=[O:37])[NH:32][C:31]([NH:38][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])=[N:30][C:29]3=4)[O:13]2)=CC=1.C(O)=O.C(O)CCC>C(Cl)Cl.CO>[OH:10][CH2:11][CH:12]1[CH:16]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:15]([O:26][CH3:27])[CH:14]([N:28]2[CH:36]=[N:35][C:34]3[C:33](=[O:37])[NH:32][C:31]([NH:38][C:39](=[O:43])[CH:40]([CH3:41])[CH3:42])=[N:30][C:29]2=3)[O:13]1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 284Formic AcidHCID 137252536HCID 137252536, compound

Product 1

HCID 136381449HCID 136381449, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 16.4 (1.5 g, 1.54 mmol) was dissolved in a mixture of 8 mL CH2Cl2 and 8 mL methanol, and treated with formic acid 16 mL. When the reaction was completed, 20 mL n-butanol was added to quench the reaction. The mixture was evaporated to dryness under reduced pressure and the byproducts were removed by washing the residue with hexane 3×200 mL. Compound 16.5 (840 mg, 92% yield) was obtained.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe byproducts were removed
  5. washby washing the residue with hexane 3×200 mL

Sources & evidence

ORD record
ord-fee15c3ddfcb41f687481e3b2b8170fd
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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