Sodium → rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamate

HRID 371216ノート

反応式

HRID 371216 の反応式
[Na].[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@@H:13]([CH3:14])[N:12](OC)[C:11]1=[O:17])=[O:8])([CH3:5])([CH3:4])[CH3:3]>N.O1CCCC1>[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@@H:13]([CH3:14])[NH:12][C:11]1=[O:17])=[O:8])([CH3:5])([CH3:3])[CH3:4]

参加物

5

反応物 2

HCID 5360545SodiumHCID 57291996Carbamic acid, (1-methoxy-2-methyl-4-oxo-3-azetidinyl)-, 1,1-dimethylethyl ester, (2R-cis)-

生成物 1

HCID 57285608rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamate収率 94.4%

試薬・触媒・溶媒 2

HCID 222Ammonia溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Sodium (1.35 g) is dissolved in about 300 ml of liquid ammonia at -50° C. and 5.87 g of (3S-cis)-3-t-Butoxycarbonylamino-1-methoxy-4-methylazetidinone in 35 ml tetrahydrofuran is added dropwise via syringe. An additional 10 ml of tetrahydrofuran is used for rinsing. Near the end of the addition about 100 mg of additional sodium is added. The mixture is stirred for five more minutes, then quenched by adding 3.35 g of solid ammonium chloride in one portion. Ammonia is blown off with a nitrogen stream and 250 ml of ethyl acetate is added to the residue. After filtration and washing the solid with ethyl acetate, the combined filtrate is stripped of solvent to give 4.82 g of the title compound.

後処理

  1. washfor rinsing
  2. additionNear the end of the addition about 100 mg of additional sodium
  3. additionis added
  4. customquenched
  5. additionby adding 3.35 g of solid ammonium chloride in one portion
  6. additionis added to the residue
  7. filtrationAfter filtration
  8. washwashing the solid with ethyl acetate

出典と根拠

ORDレコード
ord-796d948365914944b96eb7295abccb2f
出典データセット
uspto-grants-1985_07
特許番号
US04529698

反応ノート

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