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

HRID 2219777ノート

反応式

HRID 2219777 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

3-[2-Azido-2-(2-ethoxycarbonylmethoxy-ethoxy)-ethoxy]-benzoic acid (0.212 g, 0.6 mmol) was stirred with N,N′-disuccinimidyl carbonate (0.184 g, 0.72 mmol) and DMAP (0.088 g, 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-trifluoro-acetamide (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).

後処理

  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

出典と根拠

ORDレコード
ord-88f28fff07f040c98a66170ae5efd505
出典データセット
uspto-grants-2008_08
特許番号
US07414116B2

反応ノート

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