Formaldehyde → HCID 53783994、化合物

HRID 2413704ノート

反応式

HRID 2413704 の反応式
[CH2:1]=O.[O:3]=[C:4]1[NH:7][C@H:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1.[C:18](=[O:21])([OH:20])[O-:19].[Na+]>C(O)=O>[OH:19][CH2:18][N:7]1[C:4](=[O:3])[CH2:5][C@H:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH:18]([O:20][CH2:1][N:7]1[C:4](=[O:3])[CH2:5][C@H:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:21]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 717310Benzyl (2S)-4-oxoazetidine-2-carboxylate

生成物 2

HCID 53783994HCID 53783994、化合物HCID 54137886HCID 54137886、化合物

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

To a mixture of 10 ml of formic acid and 20 ml of formalin was added 3 g of (S)-benzyl 4-oxo-2-azetidine-carboxylate (14). The resulting mixture was kept at 50° C. for 15 minutes. After cooling, the mixture was made alkaline with a saturated sodium bicarbonate aqueous solution and extracted twice with 50 ml of ether. The ethereal extracts were washed with a saturated sodium chloride aqueous solution and then dried. The solvent was removed by distillation under reduced pressure and the residue thus obtained was purified by column chromatography using silica gel. Thus, 970 mg of (S)-benzyl 1-hydroxymethyl-4-oxo-2-azetidinecarboxylate (15) and 1.78 g of (S)-benzyl 1-formyloxymethyl-4-oxo-2-azetidinecarboxylate (16) were obtained.

後処理

  1. temperatureAfter cooling
  2. extractionextracted twice with 50 ml of ether
  3. washThe ethereal extracts were washed with a saturated sodium chloride aqueous solution
  4. customdried
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-36ab6e7adf9c4bbeade3b2ad4b89af76
出典データセット
uspto-grants-1988_01
特許番号
US04719207

反応ノート

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