Ethanol → HCID 67408834, compound

HRID 709878Notes

Reaction equation

HRID 709878 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C@:19]1([CH3:25])[CH2:23][O:22]C(=O)[NH:20]1)[N:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)C.[OH-].[Li+]>O>[NH2:20][C@@:19]([C:14]1[N:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:10]=2)[N:15]=1)([CH3:25])[CH2:23][OH:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 67408611HCID 67408611, compound

Product 1

HCID 67408834HCID 67408834, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(R)-4-(6-Heptyloxy-quinazolin-2-yl)-4-methyl-oxazolidin-2-one (40.0 mg, 0.000116 mol) was dissolved in ethanol (2 mL, 0.03 mol), followed by 4 M lithium hydroxide in water (1 mL). The reaction mixture was then heated at 80° C. for 2 hours. All solvent was removed. The solid was extracted with DCM, and was purified via chromatography (SiO2, 4 g, 0-100% (10% of MeOH with 2N ammonia in DCM and DCM) to give the desired product (21 mg, 57%). 1H NMR (CHLOROFORM-d) δ: 9.25 (s, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.49 (dd, J=9.7, 2.4 Hz, 1H), 7.08 (d, J=2.5 Hz, 1H), 6.60 (br. s., 3H), 4.26 (d, J=11.8 Hz, 1H), 4.17 (d, J=11.8 Hz, 1H), 4.06 (t, J=6.7 Hz, 2H), 1.81-2.00 (m, 4H), 1.77 (s, 3H), 1.43-1.61 (m, 2H), 1.20-1.43 (m, 4H), 0.84-1.01 (m, 3H). MS (ES, M+1): 318.30.

Workup

  1. customAll solvent was removed
  2. extractionThe solid was extracted with DCM
  3. customwas purified via chromatography (SiO2, 4 g, 0-100% (10% of MeOH with 2N ammonia in DCM and DCM)

Sources & evidence

ORD record
ord-e60c9eaa28a444099fa00296a15f7e12
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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