Iodine → L-Leucine

HRID 1606826노트

반응식

HRID 1606826 반응식
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([O:9]N1C(=O)CCC1=O)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(O)(C(F)(F)F)=O.CO.II>CN(C=O)C.CCN(CC)CC>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

참가 물질

7

반응물 4

HCID 807IodineHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 11089751N-[(Phenylmethoxy)carbonyl]-L-leucine 2,5-dioxo-1-pyrrolidinyl ester

생성물 1

HCID 6106L-Leucine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Z-Leu-OSu (LXIII) (10.8 gm), and the above TFA salt (LXIV) (17.8 gm) in DMF (200 mg) and Et3N (8.4 ml), were stirred at room temperature for 24 hours. The reaction mixture was evaporated in vacuo and the resulting peptide was partitioned between H2O and CHCl3. The dried (Na2SO4) organic layer was evaporated and crystallized from acetone-MeOH to afford 17.7 gm (80%) of pure LXV: m.p. 138°-140°C; [α]D22 -35.4 (c, 1.16, MeOH); Rf1 0.86 and Rf3 0.68, single spot with I2 reagent. Amino acid analysis gave Leu 1.1; Arg 0.9; Pro 1.0; Gly 1.0; NH3 0.9.

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe resulting peptide was partitioned between H2O and CHCl3
  3. dry with materialThe dried (Na2SO4) organic layer
  4. customwas evaporated
  5. customcrystallized from acetone-MeOH
  6. customto afford 17.7 gm (80%) of pure LXV

출처 및 근거

ORD 기록
ord-3a08098f79d9417c85401e9cea21e768
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953416

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