Sodium hydride → 1-Methoxymethyl-4-tritylthio-2-azetidinone

HRID 355220Notes

Reaction equation

HRID 355220 reaction equation
[C:1]([S:20][CH:21]1[NH:24][C:23](=[O:25])[CH2:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28][O:29][CH2:30]Br>C1COCC1.CO.CCOCC>[CH3:28][O:29][CH2:30][N:24]1[CH:21]([S:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][C:23]1=[O:25]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 127801644-Tritylthio-2-azetidinone

Product 1

HCID 127801611-Methoxymethyl-4-tritylthio-2-azetidinoneYield 110.4%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-tritylthio-2-azetidinone (1.38 g, 4.0 mmoles) in THF (10 ml) was added to a well stirred suspension of sodium hydride (200 mg of commercial 50%, 4.1 mmoles, washed with pentane) in THF (10 ml) maintained at -15°. Methanol (12 drops) was added and the mixture was stirred at -15° for 0.5 h. Methoxymethyl bromide (0.58 g, 4.6 mmoles) was added and the mixture was stirred for 2 h, diluted with ether, washed with water and brine, dried and concentrated to leave an oil (1.72 g). Crystallization from pentane gave a white solid (1.41 g) m.p. 72-76 δ (ppm, CDCl3): 7.3 (15H, m, aromatics), 4.4 (3H, m, NCH2O and H-4), 3.22 (3H, s, CH3), 2.76 (2H, m, H-3).

Workup

  1. temperaturemaintained at -15°
  2. stirringthe mixture was stirred at -15° for 0.5 h
  3. stirringthe mixture was stirred for 2 h
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-280a00c5d50e4398b9fd1aa90f46542c
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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