Hydrochloric Acid → 1-(4-Benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid

HRID 2269316ノート

反応式

HRID 2269316 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:30]CC1.Cl.[Li+].[OH-]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]([OH:21])[CH2:24][CH2:25][CH:19]2[C:20]([OH:30])=[O:26])(=[O:16])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 183337695-(4-Benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one

生成物 1

HCID 181794331-(4-Benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of 5-(4-benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (0.10 g, 0.26 mmol) and 2 mL of THF was added 0.2 mL of 1M aqueous HCl. After stirring for 10 min, 0.15 mL of 12M aqueous HCL was added. After stirring for 30 min, TLC indicated no detectable reaction. The mixture was then treated with 2 mL of saturated aqueous LiOH and 2 mL of methanol. After stirring for 20 min at room temperature, the mixture was acidified with 1M HCl, extracted 3× into ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo, affording 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid (0.10 g) as a colorless syrup:

後処理

  1. addition0.15 mL of 12M aqueous HCL was added
  2. stirringAfter stirring for 30 min
  3. customno detectable reaction
  4. stirringAfter stirring for 20 min at room temperature
  5. extractionextracted 3× into ethyl acetate
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e632d52bf5d64c1797d42385c7ddce13
出典データセット
uspto-grants-2001_12
特許番号
US06329397B1

反応ノート

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