Hydrochloric Acid → 3alpha-Mercaptoandrostane-6,17-dione

HRID 1912736ノート

反応式

HRID 1912736 の反応式
C([S:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[O:25])[CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=O)C.C([S-])CC.[Na+].Cl.O>CO>[SH:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[O:25])[CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 46817251-Propanethiol, sodium salt (1:1)HCID 866355963alpha-Acetylthioandrostane-6,17-dione

生成物 1

HCID 866356003alpha-Mercaptoandrostane-6,17-dione収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of 3α-acetylthioandrostane-6,17-dione (1.07 g) in MeOH (30 mL), sodium propanethiolate (0.28 g) was added and the reaction stirred for 20 minutes at room temperature. The mixture was neutralized with 1N HCl. Water was added and the mixture extracted with EtOAc. The organic layer was separated, washed with brine, and dried over Na2SO4 and evaporated to dryness to give 3α-mercaptoandrostane-6,17-dione (943 mg, 100%), used without further purification. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.54 (1H, m), 2.77 (1H, m), 2.54 (1H, d), 2.45-1.10 (19H, m), 0.78 (3H, s), 0.66 (3H, s).

後処理

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-a728cc7bb7474304b0b5f6f9d2b16db2
出典データセット
uspto-grants-2013_12
特許番号
US08609644B2

反応ノート

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