Triethylamine → 5'-O-(N-Lysylisoleucyl)-5-fluorouridine dihydrochloride

HRID 329836노트

반응식

HRID 329836 반응식
[ClH:1].[NH2:2][C@H:3]([C:8]([O:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[CH:24]=[C:23]([F:25])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[C@H:14]([OH:26])[C@@H:13]1[OH:27])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5].C(OC([NH:38][C@H:39]([C:55](O)=[O:56])[CH2:40][CH2:41][CH2:42][CH2:43][NH:44]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.C(P(C#N)(CC)=O)C.C(N(CC)CC)C>CN(C)C=O>[ClH:1].[ClH:1].[NH2:38][C@H:39]([C:55]([NH:2][C@H:3]([C:8]([O:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[CH:24]=[C:23]([F:25])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[C@H:14]([OH:26])[C@@H:13]1[OH:27])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5])=[O:56])[CH2:40][CH2:41][CH2:42][CH2:43][NH2:44]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 7269422N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysineHCID 13586794DiethylphosphorylcyanideHCID 186373305'-O-isoleucyl-5-fluorouridine hydrochloride

생성물 1

HCID 186373355'-O-(N-Lysylisoleucyl)-5-fluorouridine dihydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1.00 Gram (2.42 mmol) of 5'-O-isoleucyl-5-fluorouridine hydrochloride was dissolved in dimethylformamide (20 ml), and 1.00 g (2.85 mmol) of Nα,Nε -di-benzyloxycarbonyllysine and 0.67 g (3.69 mmol) of diethylphosphoryl cyanide were then added. To this solution was added under ice-cooling 1.54 g (15.2 mmol) of triethylamine, and the mixture was stirred overnight at room temperature. After addition of ice water the reaction liquid was extracted with chloroform (200 ml). The organic layer was dried (over Na2SO4) and concentrated under reduced pressure, and the residue was subjected to separation/purification by way of silica gel column chromatography (first time: 2.5×11 cm, chloroform containing 4% methanol; second time: 5×14 cm, a linear gradient of ethyl acetate-n-hexane (1:1) containing 0→6% methanol) whereby 0.46 g (26%) of 5'-O-{N-(Nα,Nε -di-benzyloxycarbonyllysyl)isoleucyl}-5-fluorouridine was obtained as a colorless powdery solid.

후처리

  1. additionTo this solution was added under ice-
  2. customthe reaction liquid
  3. extractionwas extracted with chloroform (200 ml)
  4. dry with materialThe organic layer was dried (over Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was subjected to separation/purification by way of silica gel column chromatography (first time
  7. additionsecond time: 5×14 cm, a linear gradient of ethyl acetate-n-hexane (1:1) containing 0→6% methanol) whereby 0.46 g (26%) of 5'-O-{N-(Nα,Nε -di-benzyloxycarbonyllysyl)isoleucyl}-5-fluorouridine
  8. customwas obtained as a colorless powdery solid

출처 및 근거

ORD 기록
ord-8f9fb969e06c4209b90c3d26cea6b72a
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892939

반응 노트

불러오는 중…