Trifluoroacetic acid → (2S)-2-amino-3-methyl-butyric acid [11beta,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester trifluoroacetate

HRID 53066

Reaktionsgleichung

Reaktionsgleichung von HRID 53066
[OH:1][C@H:2]1[CH2:37][C@@:36]2([CH3:38])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:39])[C:17](=[O:35])[CH:18]([O:20][C:21](=[O:34])[C@@H:22]([NH:26]C(OC(C)(C)C)=O)[CH:23]([CH3:25])[CH3:24])[OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:41])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:40])[CH2:6][CH2:5]1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[OH:1][C@H:2]1[CH2:37][C@@:36]2([CH3:38])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:39])[C:17](=[O:35])[CH:18]([O:20][C:21](=[O:34])[C@@H:22]([NH2:26])[CH:23]([CH3:25])[CH3:24])[OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:41])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:40])[CH2:6][CH2:5]1

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86750657(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methylbutyric acid [11beta,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester

Produkt 1

HCID 86750658(2S)-2-amino-3-methyl-butyric acid [11beta,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester trifluoroacetateAusbeute 76 %

Versuchsvorschrift

500 mg (0.89 mmol) of (2S)-2-((1,1-dimethylethoxycarbonyl) -amino)-3-methyl-butyric acid [11β,17,21-trihydroxy-3,20-dioxo -pregn-4-en-21-yl] ester (Example 27) is mixed with 1 ml of trifluoroacetic acid and stirred for 10 minutes at room temperature. Then, the trifluoroacetic acid is evaporated in a vacuum. The residue is mixed with stirring with a little diethyl ether, the white precipitate that is produced is suctioned off and dried. 385 mg (76%) of (2S)-2-amino-3-methyl-butyric acid [11β,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester trifluoroacetate is obtained.

Aufarbeitung

  1. customThen, the trifluoroacetic acid is evaporated in a vacuum
  2. additionThe residue is mixed
  3. stirringwith stirring with a little diethyl ether
  4. customthe white precipitate that is produced
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-47a2d8e4b8b645a482a9b6f8488878c1
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616573

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