I)h~)siphodiestcr~tsr~. 211so, hot ti 4 : r i d 9 common binding sit ('h.
niiisi
li:iv(s
Experimental Section All melting point- were taken on a Fihher -Johns melting poiiit :Ipparatiis and are iincorrected. 'The iiv arid ir data were obtaiiietl or! a Cnry Model 11 and Beckmarin IR-5 spectrophotometers, rwpectively. The nnir spectra were determined on a Tariaii A-BO spectrometer in CIICI, using TJIS as an internal standard ( 0 ppm). All parts pel' rnillioii values are the center of the signal-. lticroanalyses were performed b y Midn-est 1\Iicrolab, In?., Indianapolis, Tnd. Where analyses are indicated onlg b of the elements. (Table. I and TI), analytical results ob those elements were withiii 3 ~ 0 . 4 ' of the theoret,ical valiie.
General Method. Oximes. 3-Oximino-17a-acetoxypregn-4ene-3,2O-dione ( l ) . ~.\- -soliitiiiii m i i t iiiiiiiig 1 .O g of 17a-acet prngesterorie, XO nig of lIOITFl;j- .CY, :riiii 5 nil of C,H,N heated on :I ;te:trii \):it h f o i . I.,; h i , . T h e iiiisliii,e W N S poured : i large aniouiit of ire--w:itrr :uii cariitie oxime 1 hus precipitatecl w:i$ collected by filtration. 1: 1 .O g of 1 : Inp 240-2441 ': [ a ]I) 6,011 A,,, 240 m p : nnii' (CIIC'I.,)0.70 (C-21 I, 2.12 (C-17 0 . 1 C ) . . j . S ! ) (CGeneral Method. Beckmann Rearrangements. 3-Aza-17uacetoxy-A-homo-4a-pregnene-4,ZO-dione (7).--To R soliitioii r i l t i i:rinirig 4.0 g of 1 iii :Mml of piirified dioxaiie was added 5 nil of SOCl?. The inist.ii1.e its stirred :it I Y K I I I temperatiire ~ for 1.; 111, :xild poiired i i i t i i it lavge i t t i i o i i i i t of iw \yaiei'. The escess acid \v:ty iieiiii~alixetl\vi1 11 S:iTIC'O:+: i i i t l tlic - i i l i i t i i i i i w:ts estractetl Lvitli CI[?(2!. T h c l oi.g:iiiir 1 : i y ~ rw : t y w:iiheti ( f T 2 0 I , dried (SH?~ 0 4:rritl ) , filti!reil. Thr filtixtcl\v:L< cv:ipui,:iicvl t o give it broe-ii oil \vhirh c,oiil(l be i,ei.i.~-,t:illizc,tl froni :ic~~~t~)iic~-Iiex:~~~e t o give 1 ,-l K 8 : nip 2 7 4 27;": [ a i +~.i.!)": x,'~!Y X I , >.7.j, x s n 6.0; p : P P I n i p : 1i1nr ( C I ) C ~ :().ti; ~ J ppni ( ( ' - I & ) , I . I > (('-IO),
s 3
4 a . X = C1. K = .A
