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Hydrochloric Acid → Cholan-24-oic acid, 3-(acetyloxy)-7-oxo-, methyl ester, (3alpha,5beta)-

HRID 346116
ノート
印刷プレビュー

反応式

HRID 346116 の反応式
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.[C:30](OC(=O)C)(=[O:32])[CH3:31].C(N(CC)CC)C.Cl>C(Cl)Cl.O.N1(C2C=CN=CC=2)CCCC1>[C:30]([O:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)(=[O:32])[CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 99310883alpha-Hydroxy-7-oxo-5beta-cholan-24-oic acid methyl ester

生成物 1

HCID 18647600Cholan-24-oic acid, 3-(acetyloxy)-7-oxo-, methyl ester, (3alpha,5beta)-収率 95.1%

試薬・触媒・溶媒 3

HCID 75567
4-Pyrrolidinopyridine
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of methyl 3α-hydroxy-7-keto-5β-cholanoate (10 g, 24.72 mmoles) in methylene chloride (40 ml) was added with acetic anhydride (3.79 g, 37.1 mmoles), triethylamine (3.63 g, 36 mmoles) and 4-pyrrolidino-pyridine (0.11 g, 0.74 mmoles) and the reaction mixture was left to react for 3 hours under strong magnetic stirring, then it was diluted with methylene chloride (50 ml) and water (50 ml) and acidified with 10% hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with methylene chloride (3×20 ml). The combined organic phases were washed with brine (1×30 ml), dried over sodium sulfate and concentrated under vacuum. The residue (11.0 g) was subjected to flash chromatography on silica, eluting with methylene chloride/methanol 99:1, to obtain 10.5 g of a pure product (95%).

後処理

  1. waitthe reaction mixture was left
  2. customto react for 3 hours under strong magnetic stirring
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with methylene chloride (3×20 ml)
  5. washThe combined organic phases were washed with brine (1×30 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. washeluting with methylene chloride/methanol 99:1

出典と根拠

ORDレコード
ord-e5fd80242a814c7fb3c1801726c648ba
出典データセット
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05061701

反応ノート

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