Hydrochloric Acid → (R)-Dihydrolipoic acid

HRID 1068534

反応式

HRID 1068534 の反応式
S1C=CCS1.[CH2:6]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:9][S:8][CH2:7]1.[BH4-].[Na+].Cl>C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1.O>[CH2:12]([CH2:11][C@@H:10]([SH:9])[CH2:6][CH2:7][SH:8])[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6112Lipoic acid2 回HCID 5253311,2-DithioleHCID 4311764Sodium borohydride

生成物 1

HCID 9834298(R)-Dihydrolipoic acid収率 80%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

The synthesis of a bidentate dithiol ligand was accomplished via the reduction of the coenzyme lipoic acid. The general procedure was described in I. C. Gunsalus, L. S. Barton, W. Gruber, J. Am. Chem. Soc. 78:1763-1766 (1956). Sodium borohydride (1.2 g) was added in 30-50 mg portions to a stirring suspension of lipoic acid (6.0 g) in 117 mL of 0.25 M sodium bicarbonate in 0° C. water. The reaction was stirred for 45 minutes at 0° C., after which 100 mL toluene was added and the mixture was acidified to pH˜2 with hydrochloric acid. The toluene layer was collected and saved. The aqueous layer was washed three times with 15 mL toluene. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum, leaving behind the product dihydrolipoic acid as a yellow oil (yield 80%).

後処理

  1. customThe toluene layer was collected
  2. washThe aqueous layer was washed three times with 15 mL toluene
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-5e69ae8e86d84abfacdbcd6af546474b
出典データセット
uspto-grants-2001_06
特許番号
US06251303B1

関連ノート

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