Hydrochloric Acid → HCID 22225525, compound

HRID 2223235Notes

Reaction equation

HRID 2223235 reaction equation
[CH2:1]([O:8][N:9]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:10]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:19].Cl>C1COCC1.O.CO>[CH2:1]([O:8][NH:9][CH2:12][CH:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:10]([OH:18])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68831760HCID 68831760, compound

Product 1

HCID 22225525HCID 22225525, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To 1-benzyloxy-3-pentylazetin-2-one (1.82 g, 7.37 mmol) in a mixture of THF—H2O-MeOH (100 mL, 3:1:1 v/v) was added LiOH monohydrate (3.60 g, 73.68 mmol). After stirring at room temperature overnight, water (50 mL) was added to the mixture. The solution was acidified to pH 6 with 3N HCl and extracted with EtOAc (100 mL×2). The combined organic layers were dried over MgSO4, and evaporated under vacuum to yield the title compound (1.60 g, 82%). 1H NMR (400 MHz, CHCl3) δ 9.80 (br s, 1H), 7.37 (m, 5H), 4.75 (m, 2H), 3.14 (m, 2H), 2.74 (m, 1H), 170 (m, 1H), 1.53 (m, 1H), 1.38–1.25 (m, 6H), 0.91 (t, J=6.8 Hz, 3H). MH+ 266.

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-e68ff32e6eb246f7a9c72003dc4d6089
Source dataset
uspto-grants-2008_05
Patent number
US07375120B2

Reaction notes

Loading…