Pivaloyl chloride → N-{3-[4-(chloroacetyl)phenyl]propionyl} alanine methyl ester

HRID 2419372노트

반응식

HRID 2419372 반응식
C(Cl)(=O)C(C)(C)C.[Cl:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:14][CH:13]=1)=[O:11].Cl.[CH3:24][O:25][C:26](=[O:30])[CH:27]([CH3:29])[NH2:28].C(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.CN(C)C=O.C(N(CC)CC)C>[CH3:24][O:25][C:26](=[O:30])[C@H:27]([CH3:29])[NH:28][C:20](=[O:22])[CH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[CH2:9][Cl:8])=[CH:17][CH:16]=1

참가 물질

9

반응물 4

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 2756298Alanine, methyl ester, hydrochloride (1:1)HCID 203155713-[4-(Chloroacetyl)phenyl]propionic acid

생성물 1

HCID 53760308N-{3-[4-(chloroacetyl)phenyl]propionyl} alanine methyl ester

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매2회

반응 조건

온도
-15 °C

실험 절차

A solution of pivaloyl chloride (4.41ml.) in tetrahydrofuran (30ml.) was added to a stirred solution, cooled to -15° C., of 3-[4-(chloroacetyl)phenyl]propionic acid (9.7g.) and triethylamine (5.5ml.) in tetrahydrofuran (30ml.) and acetonitrile (40ml.). The resultant mixture was stirred for one hour at -15° C. A suspension of DL-alanine methyl ester hydrochloride (5.0g.) in dimethylformamide (30ml.) containing triethylamine (5.5ml.) was then added over 15 minutes. The mixture was stirred at -15° C. for 1 hour and then for 16 hours at room temperature. Saturated sodium bicarbonate solution (30ml.) was added and the solution was stirred for 30 minutes and then evaporated in vacuo. The residue was mixed with water (150ml.) and was extracted with chloroform (2 × 100ml.). The extracts were washed successively with 10% hydrochloric acid (200ml.), water (200ml.), saturated sodium bicarbonate solution (200ml.) and water (200ml.), dried (MgSO 4) and evaporated. The residue was recrystallised from toluene/petrol to give N-{3-[4-(chloroacetyl)phenyl]propionyl} alanine methyl ester, m.p. 122°-124° C.

후처리

  1. additionwas then added over 15 minutes
  2. waitfor 16 hours at room temperature
  3. stirringthe solution was stirred for 30 minutes
  4. customevaporated in vacuo
  5. additionThe residue was mixed with water (150ml.)
  6. extractionwas extracted with chloroform (2 × 100ml.)
  7. washThe extracts were washed successively with 10% hydrochloric acid (200ml.), water (200ml.), saturated sodium bicarbonate solution (200ml.) and water (200ml.)
  8. dry with materialdried (MgSO 4)
  9. customevaporated
  10. customThe residue was recrystallised from toluene/petrol

출처 및 근거

ORD 기록
ord-9a71e656c3604e6fbaef698fa778409f
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04105790

반응 노트

불러오는 중…