Acetic Anhydride → HCID 15542237, compound

HRID 1603359Notes

Reaction equation

HRID 1603359 reaction equation
[F:1][C:2]([F:42])([C:38]([F:41])([F:40])[F:39])[CH2:3][CH2:4][CH2:5][S:6][CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:35][C:34]2[CH:33]=[C:32]([OH:36])[CH:31]=[CH:30][C:29]=2[C@@H:28]2[C@@H:19]1[C@H:20]1[C@@:24]([CH2:26][CH2:27]2)([CH3:25])[C@@H:23]([OH:37])[CH2:22][CH2:21]1.C(OC(=O)C)(=O)C.B1([O-])OO1.[OH2:54].[OH2:55].O.O.[Na+]>>[F:42][C:2]([F:1])([C:38]([F:39])([F:40])[F:41])[CH2:3][CH2:4][CH2:5][S:6]([CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:35][C:34]2[CH:33]=[C:32]([OH:36])[CH:31]=[CH:30][C:29]=2[C@@H:28]2[C@@H:19]1[C@H:20]1[C@@:24]([CH2:26][CH2:27]2)([CH3:25])[C@@H:23]([OH:37])[CH2:22][CH2:21]1)(=[O:55])=[O:54]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 15542228HCID 15542228, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 15542237HCID 15542237, compound

Procedure

Under the conditions of Example 3, 76 mg of 7α-{5-[(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidin-1-yl]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol (Example 26f) is acetylated with acetic anhydride, and the crude product is oxidized, as described in Example 4, with sodium perborate tetrahydrate, worked up and chromatographed. 31 mg of the title compound is obtained as oil. [α]D22 =30.6° (c=0.515 in methanol).

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-9937a36562a44407a77920490f48351b
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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