Benzyl Bromide → (s)-2-Benzyloxy-4-benzyloxycarbonylaminobutyric acid

HRID 1685918

반응식

HRID 1685918 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@H:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-2].[Ba+2].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(Cl)(Cl)Cl.Cl.O.C(O)(=O)C.C(OCC)(=O)C>[CH2:32]([O:18][C@@H:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:15]([OH:17])=[O:16])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

11

반응물 4

HCID 7498Benzyl BromideHCID 2733930(S)-2-Hydroxy-4-(((phenylmethoxy)carbonyl)amino)butyric acidHCID 9855530Barium Oxide Nanoparticle Dispersion2회HCID 17749109Barium hydroxide, octahydrate

생성물 1

HCID 57784532(s)-2-Benzyloxy-4-benzyloxycarbonylaminobutyric acid

시약·촉매·용매 6

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 962Water용매2회HCID 6212Chloroform용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(S)-4-Benzyloxycarbonylamino-2-hydroxybutyric acid (5.25 g, 20.7 mmol) synthesized according to the report of Kawaguchi et al. (Journal of Antibiotics, Vol. 25, pp. 695-708 (1972)) was dissolved in 60 mL of N,N-dimethylformamide. Barium oxide (15.9 g, 103.7 mmol) was added under an ice bath. After the elapse of 2 min from the addition of barium oxide, barium hydroxide octahydrate (13.4 g, 42.5 mmol) was added thereto under an ice bath. After 10 min, benzyl bromide (7.5 mL, 63.1 mmol) was added thereto under an ice bath. After 5 min, the reaction solution was returned to room temperature and was vigorously stirred. After 1.5 hr, the completion of the reaction was confirmed by TLC (developing solvent system=chloroform:ethyl acetate:acetic acid=10:5:1), and water (0.5 mL) was added thereto under an ice bath. The mixture was diluted with chloroform (165 ml), and 4 N HCl (70 mL) was added thereto. Further, water (25 mL) was added followed by separation. The water layer was extracted with chloroform (50 mL). The organic layer and the extracted organic layer were combined and were washed with a saturated aqueous NaCl solution. The washed solution was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel (silica gel 60, neutral spheres, 160 g) (chloroform: ethyl acetate=4:1→chloroform:methanol=10:1→chloroform:methanol acetic acid=10:1:0.1 (600 mL)) to give (S)-2-benzyloxy-4-benzyloxycarbonylaminobutyrylic acid (2.86 g, 8.34 mmol).

후처리

  1. additionwas added
  2. waitAfter 5 min
  3. customwas returned to room temperature
  4. waitAfter 1.5 hr
  5. additionwas added
  6. additionwas added
  7. customfollowed by separation
  8. extractionThe water layer was extracted with chloroform (50 mL)
  9. washwere washed with a saturated aqueous NaCl solution
  10. dry with materialThe washed solution was dried over magnesium sulfate
  11. customThe solvent was removed by distillation under the reduced pressure
  12. customthe residue was purified by column chromatography on silica gel (silica gel 60, neutral spheres, 160 g) (chloroform: ethyl acetate=4:1→chloroform:methanol=10:1→chloroform:methanol acetic acid=10:1:0.1 (600 mL))
  13. customto give (S)-2-benzyloxy-4-benzyloxycarbonylaminobutyrylic acid (2.86 g, 8.34 mmol)

출처 및 근거

ORD 기록
ord-22241f15780d4867a6fe7dd69547c09d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148504B2

연결된 노트

불러오는 중…