1702
Vol. 76
NOTES
Anal. Calcd. for CihHzoOaNz: C, 63.61; Found: C, 63.46; H, 7.68. JOHN HARRISON LABORATORY OF CHEMISTRY UNIVERSITYOF PENNSYLVANIA PHILADELPHIA 4,PENNSYLVANIA
H, 7.63.
p- [ (2-Amino-4-hydroxy-6-pteridylmethyl)-p'nitrobenzenesulfonylamino ]-benzoic Acid and Intermediates BY BARNEYT MAGERLEIN AND DAVIDI. RECEIVED DECEMBER 9, 1953
WEISBLAr
Recently the synthesis of pteroylglutamic acid was described in which the amino group Of the P aminobenzoylglutamic portion was protected by a tosyl group until after the formation of the pteridine nucleus.i This note describes the synthesis of cryst a l h e P - I(2-amino-4-hydroxy-6-pteridq.lmethvl) p'-nitrobenzenesulfonylamino]-benzoic acid (VII) and its glutamic acid analog VIIa (Chart I ) . The H
I
Ii-Xs I
I
H
2
p! 1'
1, CHz-CH-CH20Ac /O\
I COOEt I
,l.
COOEt I
0-C-NH-CH
--f
2, S a O H
A I
COOH V
7"
S-CHz-CH-CH
'/
\
I
S-CHr-CH-CH2OII
iI
I
OH
S S
I
S--sS
NS
I S-XS I
Experimental Ethyl N-p'-Nitrobenzenesulfonyl-p-aniinobenzoate( I ):One hundred grams of p-nitrobenzenesulfonyl chloride was added to 71 g. of ethyl paminobenzoate dissolved in 202 ml. of 2,1-lutidine a t such a rate that the ternperaoture did not exceed 80". The solution !vas heatrd a t 8n for 45 minutes and poured with stirring onto 600 ml. of ice and water. The crude product K ~ S collected b). filtration, washed, and dried. It weighed 1.55 g. I
