Trifluoroacetic acid → [2-(1-Azido-2-{3-[2-(2,2,2-trifluoroacetylamino)-ethylcarbamoyl]phenoxy}ethoxy)ethoxy]acetic acid ethyl ester

HRID 1923448노트

반응식

HRID 1923448 반응식
[N:1]([CH:4]([O:16][CH2:17][CH2:18][O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O)=[N+:2]=[N-:3].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.FC(F)(F)C(O)=O.[NH2:51][CH2:52][CH2:53][NH:54][C:55](=[O:60])[C:56]([F:59])([F:58])[F:57].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][O:19][CH2:18][CH2:17][O:16][CH:4]([N:1]=[N+:2]=[N-:3])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:9]([C:10](=[O:12])[NH:51][CH2:52][CH2:53][NH:54][C:55](=[O:60])[C:56]([F:59])([F:58])[F:57])[CH:8]=1)[CH3:25]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 229755N-(2-aminoethyl)-2,2,2-trifluoroacetamideHCID 676246Di(succinimido) carbonateHCID 597717713-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acid

생성물 1

HCID 59771759[2-(1-Azido-2-{3-[2-(2,2,2-trifluoroacetylamino)-ethylcarbamoyl]phenoxy}ethoxy)ethoxy]acetic acid ethyl ester수율 86.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

3-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acid (0.212 g, 0.6 mmol) was stirred with N,N′-disuccinimidyl carbonate (0.184 g, 0.72 mmol) and DMAP (0.088g, 0.72 mmol) in dry DMF (1 ml) at room temperature. After 10 minutes, trifluoroacetic acid salt of N-(2-amino-ethyl)-2,2,2-trifluoroacetamide (0.194 g, 0.72 mmol) was added followed by diisopropylethylamine (DIPEA) (0.251 ml, 1.44 mmol). The reaction mixture was then stirred at room temperature for 17 hours. All the solvents were evaporated under reduced pressure and the residues were partitioned between DCM (50 ml) and aqueous NaH2PO4 (1 N, 50 ml). The aqueous layer was further extracted with DCM (2×25 ml). All the DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography (1×20 cm). The title compound, eluted with 1% methanol in DCM, was obtained as an oil (0.255 g, 86.6%). ES-MS, m/z 490.10 (M−1).

후처리

  1. customAll the solvents were evaporated under reduced pressure
  2. customthe residues were partitioned between DCM (50 ml) and aqueous NaH2PO4 (1 N, 50 ml)
  3. extractionThe aqueous layer was further extracted with DCM (2×25 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (1×20 cm)
  7. washThe title compound, eluted with 1% methanol in DCM

출처 및 근거

ORD 기록
ord-6b3503c1d9af4a9eb4bfef0735859596
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178360B2

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