l-chlorosulfonyl-3,5-dihydro-4,5-dimethyl-2-pyridone (52) was hydrolyzed and worked up in a manner similar to 43 -49. 7 lactam 56 crystallized from the hydrolysis mixture after 2 weeks standing in a freezer ( -15°). Several sublimations at 80°( 0.3 mm) afforded analytically pure 56: mp 96-98°; ir (KBr) 1325 (7.55) and 1660 cm-' (6.02 µ) (C=0); nmr (CDCls) 8.65 (mound, 1, NH), 3.87 (mound, 2, CH2NH), 2.89 (mound, 2, CH2CO), 1.67 (s, 6, CH3). Unlike lactam 49, the signals did not sharpen up after a D20 wash.
Anal. Calcd. for C I~H~~N~O : C, 70.56; H, 7.90. Found: C, 70.23; H, 7.71. Ethylacetylaminomalonate (1.03 g.) was added to a solution of sodium (0.11 g.) in dry ethanol (11 ml.) with stirring a t room temperature. 6-Methoxygramine (1.03 g. ) was then added to the mixture which was then cooled to 0' and dimethyl sulfate (0.94 ml.) added. After stirring overnight a t room temperature the mixture was added to ice and the product crystallized out (1.56 g.). The analytical sample was crystallized from ethanol to yield colorless prisms of ethyl-cu-acetamido-a-carbethoxy-,9-(3-(6-metlioxyindole))-propionate, m.p. 147-148".Anal. Calcd. for C18H24N~06: C, 59.33; H.6.64. Found: C, 59.68; H, 6.38.This ester (1.56 g.) was refluxed with lOyo sodium hydroxide solution (10 ml.) for 1 hr., then cooled and acidified with concentrated hydrochloric acid and the malonic acid derivative filtered off and washed with cold water. The residue was refluxed with water (40 ml.) for 6 hr., then sodium hydroxide (3.0 g.) added and the mixture refluxed overnight. The solution was then made acidic with 2 N sulfuric acid and then basic to phenolphthalein with barium hydroxide solution. The mixture was filtered and the filtrate evaporated to dryness in vacuo. The residue was dissolved in boiling acetic acid (40 ml.), filtered and benzene (40 ml.) added when 6-methoxytryptophan acetate (0.76 g., 42% yield from the formaldehyde-C14
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