Trifluoroacetic acid → (S)-2-Amino-3-(4-iodophenyl)propanamide

HRID 600290ノート

反応式

HRID 600290 の反応式
C(OC([NH:8][C:9](=[O:20])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)[NH2:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C@@H:10]([C:9]([NH2:8])=[O:20])[NH2:11])=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67269262N-(tert-Butoxycarbonyl)-4-iodo-(L)-phenylalaninamide

生成物 1

HCID 447705(S)-2-Amino-3-(4-iodophenyl)propanamide収率 95.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-(tert-Butoxycarbonyl)-4-iodo-(L)-phenylalaninamide (4.24 g) was dissolved in DCM (20 mL) and to the solution was added TFA (20 mL). The reaction mixture was stirred, at room temperature, for 0.5 h then concentrated to dryness under reduced pressure. The crude material obtained was loaded onto an SCX cartridge. Non-basic impurities were washed off with a 1:1 mixture of DCM and methanol, then the cartridge was eluted with 10% ammonia in methanol. Eluent from the latter was concentrated to dryness to give the free base of the sub-title compound (3 g) as a white solid.

後処理

  1. concentrationthen concentrated to dryness under reduced pressure
  2. customThe crude material obtained
  3. washNon-basic impurities were washed off with a 1:1 mixture of DCM and methanol
  4. washthe cartridge was eluted with 10% ammonia in methanol
  5. concentrationEluent from the latter was concentrated to dryness

出典と根拠

ORDレコード
ord-4aa6646318344b6c81f9321ecd07d11b
出典データセット
uspto-grants-2011_03
特許番号
US07902181B2

反応ノート

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