4-Methylmorpholine → t-butoxycarbonyl-N-(5-methoxy-5-oxopentyl)-L-phenylalaninamide

HRID 746225

반응식

HRID 746225 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[NH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 13672034Methyl 5-aminopentanoate hydrochloride

생성물 1

HCID 13385868t-butoxycarbonyl-N-(5-methoxy-5-oxopentyl)-L-phenylalaninamide수율 96.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a cold (ca -30°), stirred solution of 26.5 g (0.1 mole) of t-butoxycarbonylphenylalanine (BOC-Phe) and 11.2 g (0.1 mole) of N-methylmorpholine in 150 ml of dimethylformamide (DMF) was added dropwise 13.2 ml (0.1 mole) of isobutylchloroformate. After warming and then holding the temperature at ca. -15° for about ten minutes, the solution was recooled to ca. -39°. To the cold mixture was added additional N-methylmorpholine (12.3 ml, ca. 0.11 mole), followed by 18.5 g (0.11 mole) of methyl 5-aminopentanoate hydrochloride. The mixture was allowed to warm to room temperature and to stand overnight. Solvent and other volatiles were removed by concentration in vacuo. The residue was triturated with ethyl acetate, which was then washed successively with water, 0.5 M potassium bisulfate, water, and again with 0.5 M potassium bisulfate, and then dried over magnesium sulfate, filtered, and concentrated to a white solid. After collection, the white solid was washed thoroughly with Skellysolve B to give 36.4 g of the title compound, m.p. 98°-100°. Recrystallization from ethyl acetate/Skellysolve B afforded analytically pure crystals.

후처리

  1. temperatureAfter warming
  2. customat ca. -15°
  3. customfor about ten minutes
  4. customwas recooled to ca. -39°
  5. customSolvent and other volatiles were removed by concentration in vacuo
  6. customThe residue was triturated with ethyl acetate, which
  7. washwas then washed successively with water, 0.5 M potassium bisulfate, water
  8. dry with materialagain with 0.5 M potassium bisulfate, and then dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a white solid
  11. customAfter collection
  12. washthe white solid was washed thoroughly with Skellysolve B

출처 및 근거

ORD 기록
ord-7f0f9a9c1b0246ae910883ec4a163817
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04603121

연결된 노트

불러오는 중…