Acetic Anhydride → HCID 15542237, compound

HRID 650367Notes

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

Reactant 3

HCID 7918Acetic Anhydride

HCID 15542228HCID 15542228, compound

HCID 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

customchromatographed

Sources & evidence

ORD record: ord-1b1f7a5e955f41bdaac43e365c0acba1
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271403B1

Reaction notes

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