Sodium Chloride → HCID 86739724、化合物

HRID 1632943ノート

反応式

HRID 1632943 の反応式
[CH3:1][C:2]([CH3:14])([O:4][C:5]([NH:7][C@H:8]1[C@@H:11]([CH3:12])[NH:10][C:9]1=[O:13])=[O:6])[CH3:3].C([Li])CCC.[P:20](Cl)(=[O:25])([O:23][CH3:24])[O:21][CH3:22].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:12][C@H:11]1[N:10]([P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22])[C:9](=[O:13])[C@H:8]1[NH:7][C:5]([O:4][C:2]([CH3:1])([CH3:14])[CH3:3])=[O:6]

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 101863Phosphorochloridic acid, dimethyl esterHCID 57285608rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamateHCID 178418339Butyllithium

生成物 1

HCID 86739724HCID 86739724、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(3S-cis)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-azetidinone (918 mg) dissolved in dry tetrahydrofuran (25 ml) was cooled to -78° C. under an inert atmosphere and 1.56 M n-butyl lithium (3 ml) was added while stirring. After thirty minutes dimethyl phosphorochloridate (3.0 ml) was added and the mixture was stirred at -78° C. for 2 hours. Saturated sodium chloride solution (20 ml) was added and the mixture allowed to warm to room temperature and extracted three times with 30 ml ethyl acetate portions. The combined extracts were dried (Na2SO4) and solvent was removed in vacuo yielding an oil. Chromatography of the oil dissolved in 4 ml of ethyl acetate on a 34 g silica gel column eluting with ethyl acetate yielded 875 mg of the title compound.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at -78° C. for 2 hours
  3. extractionextracted three times with 30 ml ethyl acetate portions
  4. dry with materialThe combined extracts were dried (Na2SO4) and solvent
  5. customwas removed in vacuo
  6. customyielding an oil
  7. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-5a71a18867ce4f2a91900836a3c043c3
出典データセット
uspto-grants-1984_10
特許番号
US04478749

反応ノート

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