Chlorotrimethylsilane → HCID 57286878, compound

HRID 477460Notes

Reaction equation

HRID 477460 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([C@H:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[S:11])[CH3:9])[N:6]([CH2:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[C:5]1=[O:25])[CH3:3].Cl[Si:27]([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:28][Si:27]([CH3:30])([CH3:29])[O:1][C@@H:2]([C@@H:4]1[C@@H:7]([C@H:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[S:11])[CH3:9])[N:6]([CH2:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[C:5]1=[O:25])[CH3:3]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 57301775HCID 57301775, compound

Product 1

HCID 57286878HCID 57286878, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(3S,4S)-3-[(1R)-1-Hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-allyloxycarbonylmethyl-2-azetidinone (content, 90.6%; 14.7 g) was dissolved in dry toluene (60 ml), and chlorotrimethylsilane (7.8 g) and triethylamine (7.8 g) were added thereto under ice-cooling, followed by stirring at room temperature for 40 minutes. The reaction mixture was diluted with toluene (300 ml), washed with 2% sodium bicarbonate solution (300 ml) and aqueous sodium chloride (300 ml×2) and dried over magnesium sulfate to give (3S,4S)-3-[(1R)-1-trimethylsilyloxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-allyloxycarbonylmethyl-2-azetidinone (16.35 g; yield, 90%).

Workup

  1. temperatureunder ice-cooling
  2. washwashed with 2% sodium bicarbonate solution (300 ml) and aqueous sodium chloride (300 ml×2)
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-e51455dd9b624ad0ad6c774db0990b2d
Source dataset
uspto-grants-1989_12
Patent number
US04888344

Reaction notes

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