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

HRID 1680326Notes

Reaction equation

HRID 1680326 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 2h, 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. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c3a1eed6b9d44d4ae03996a7fceca50
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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