Trimethylsilyldiazomethane → Methyl 3-[2-(2-{2-[2-(2-iodoacetylamino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate

HRID 446645노트

반응식

HRID 446645 반응식
C1C(=O)N([O:8][C:9]([CH2:11][I:12])=O)C(=O)C1.[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].[CH3:31][Si](C=[N+]=[N-])(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.C(O)(=O)C.CO>[I:12][CH2:11][C:9]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:8]

참가 물질

9

반응물 4

HCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 3299230Iodoacetic acid N-hydroxysuccinimide esterHCID 22731902Amino-PEG4-acid

생성물 1

HCID 86671288Methyl 3-[2-(2-{2-[2-(2-iodoacetylamino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

117.4 mg of N-hydroxysuccinimidyl iodoacetate in solution in 3 ml of DCM are added to 100 mg of 3-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)propanoic acid. After 2 h at AT, 330 μl of MeOH are added and the mixture is cooled to 0° C. 360 μl of a 2M solution of trimethylsilyldiazomethane in hexane are added. After 1 h, the mixture is neutralized by addition of 50 μl of acetic acid and then a saturated aqueous NaHCO3 solution is added until pH=8 is obtained. The organic phase is dried over MgSO4 and concentrated under RP, and the residue is purified by flash chromatography on silica (Interchrom Puriflash Silica 15/35U 10G) using a gradient from 0 to 10% of methanol in DCM. 132 mg of methyl 3-[2-(2-{2-[2-(2-iodoacetylamino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate are thus obtained.

후처리

  1. customis obtained
  2. dry with materialThe organic phase is dried over MgSO4
  3. concentrationconcentrated under RP
  4. customthe residue is purified by flash chromatography on silica (Interchrom Puriflash Silica 15/35U 10G)

출처 및 근거

ORD 기록
ord-502cb843f07243369ff56202f0bbb50d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481042B2

반응 노트

불러오는 중…