N-methyl-2-pyrrolidone → 3-Hydroxy-alpha-methyl-L-tyrosine 1-(2,2-dimethyl-1-oxopropoxy)ethyl ester

HRID 1906986

반응식

HRID 1906986 반응식
[CH3:1][C@@:2]([NH2:15])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([OH:10])[CH:9]=1.[Br-].[Li+].CN1CCCC1=O.[C:25]([O:31][CH:32](Cl)[CH3:33])(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C(OCC)(=O)C>[OH:10][C:8]1[CH:9]=[C:4]([CH2:3][C@@:2]([CH3:1])([C:12]([O:14][CH:32]([O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:33])=[O:13])[NH2:15])[CH:5]=[CH:6][C:7]=1[OH:11]

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 38853MethyldopaHCID 82050Lithium BromideHCID 30161741-Chloroethyl pivalate

생성물 1

HCID 881263-Hydroxy-alpha-methyl-L-tyrosine 1-(2,2-dimethyl-1-oxopropoxy)ethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

10 grams (0.047 mole) of α-methyldopa, 4.7 grams of powdered 4A molecular sieves, 6.1 grams (0.070 mole) of lithium bromide and 47 milliliters of N-methylpyrrolidinone were stirred for about one hour at 25° C. To this mixture, 8.1 grams (0.049 mole) of α-chloroethyl pivalate was added and the mixture was aged at 55° C. for 8 hours. At the end of this time, the mixture was cooled to 25° C., diluted with 100 milliliters of ethyl acetate and washed successively with one 200 milliliter and two 100 milliliter portions of saturated sodium bicarbonate solution. The combined sodium bicarbonate washes were extracted with two 100 milliliter portions of ethyl acetate and the combined ethyl acetate extracts concentrated under vacuum to 150 milliliters. The assay yield of α-pivaloyloxyethyl (S)-3-(3,4-dihydroxyphenyl)-2-methylalaninate was found to be 14.4 grams or 90 percent of theoretical.

후처리

  1. waitthe mixture was aged at 55° C. for 8 hours
  2. temperatureAt the end of this time, the mixture was cooled to 25° C.
  3. washwashed successively with one 200 milliliter and two 100 milliliter portions of saturated sodium bicarbonate solution
  4. extractionThe combined sodium bicarbonate washes were extracted with two 100 milliliter portions of ethyl acetate
  5. concentrationthe combined ethyl acetate extracts concentrated under vacuum to 150 milliliters

출처 및 근거

ORD 기록
ord-e6e58058f4af4af3a05bd51fad74b2f4
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04654433

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