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

HRID 42133노트

반응식

HRID 42133 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 866356003alpha-Mercaptoandrostane-6,17-dione수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8c6096ebfeaa428da189992164337d37
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536160B2

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