Methoxyacetic Acid → HCID 15382175, compound

HRID 1858348Notes

Reaction equation

HRID 1858348 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2.[CH3:25][O:26][CH2:27][C:28](O)=[O:29]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][C:28](=[O:29])[CH2:27][O:26][CH3:25])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 12251Methoxyacetic AcidHCID 10860472HCID 10860472, compound

Product 1

HCID 15382175HCID 15382175, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (2.0 g, 6.1 mmol) and 4-dimethylaminopyridine (0.8 g, 6.5 mmol) were dissolved in absolute CH2Cl2 (20 ml) and methoxy acetic acid (6.1 mmol) was added dropwise whilst cooling with ice and the resulting mixture was stirred for 2 hours at this temperature. The reaction mixture was poured onto water (50 ml), the organic phase was washed twice more with 30 ml of water and dried over MgSO4. The solvent was evaporated off and the residue separated by flash chromatography (CH2Cl2 /MeOH 9/1).

Workup

  1. temperaturewhilst cooling with ice
  2. additionThe reaction mixture was poured onto water (50 ml)
  3. washthe organic phase was washed twice more with 30 ml of water
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated off
  6. customthe residue separated by flash chromatography (CH2Cl2 /MeOH 9/1)

Sources & evidence

ORD record
ord-9e5dbdcfb5ed414b8c50ee5cd1850119
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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