Triethylamine → 16-Methylene-17-hydroxypregna-1,4,9(11)-triene-3,20-dione

HRID 1285316ノート

反応式

HRID 1285316 の反応式
C[O:2]P(OC)OC.C(N(CC)CC)C.C1(S([CH2:23][C:24]2[C@@H:25]([C@:29]3([CH3:46])[C@@H:42]([CH:43]=2)[C@H:41]2[C:32]([C@:33]4([CH3:45])[C:38]([CH2:39][CH2:40]2)=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]4)=[CH:31][CH2:30]3)[C:26](=[O:28])[CH3:27])=O)C=CC=CC=1>C1(C)C=CC=CC=1.CO>[OH:2][C@:25]1([C@:29]2([CH3:46])[C@H:42]([C@H:41]3[C:32](=[CH:31][CH2:30]2)[C@:33]2([CH3:45])[C:38](=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]2)[CH2:39][CH2:40]3)[CH2:43][C:24]1=[CH2:23])[C:26](=[O:28])[CH3:27]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 18601425HCID 18601425、化合物

生成物 1

HCID 308215016-Methylene-17-hydroxypregna-1,4,9(11)-triene-3,20-dione

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

Trimethylphosphite (0.3 ml) and triethylamine (0.3 ml) are added to a solution of 16(phenylsulfinylmethyl)pregn-1,4,9(11),15-tetraene-3,20-dione (VIB, Example 18, 538 mg of the mixed isomers) in toluene (5 ml) and methanol (0.7 ml). The mixture was heated at 85° in a sealed vial until the reaction was complete. The reaction mixture was poured into a buffer solution and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulfate, and concentrated to a solid which is recrystallized from ethyl acetate to give the title compound. NMR (CDCl3) 0.70, 1.36, 2.26, 5.10, 5.51, 6.00, 6.20 and 7.17 δ.

後処理

  1. temperatureThe mixture was heated at 85° in a sealed vial until the reaction
  2. additionThe reaction mixture was poured into a buffer solution
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a solid which
  8. customis recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-541f6c4197304912a224ad5390c641f9
出典データセット
uspto-grants-1986_01
特許番号
US04567001

反応ノート

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