Serinol → BOC-D-Ala-SerOH

HRID 36578

반응식

HRID 36578 반응식
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N([OH:25])N=NC=2C=1.[NH:26]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:27]([C:29]([OH:31])=O)[CH3:28].[NH2:39][CH:40]([CH2:43][OH:44])[CH2:41][OH:42]>>[NH:26]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:27]([C:29]([NH:39][C@H:40]([C:43]([OH:25])=[O:44])[CH2:41][OH:42])=[O:31])[CH3:28]

참가 물질

4

반응물 3

HCID 68294SerinolHCID 637606BOC-D-alanineHCID 21712060DCCI HOBt

생성물 1

HCID 131719002BOC-D-Ala-SerOH

실험 절차

BOC-D-Ala-SerOH was prepared on a 1.0 mMol-scale by the DCC-HOBT mediated condensation of BOC-D-Ala and serinol following the procedure described in Example 21. The crude reaction product was purified by chromatography on a 1.7×24 cm column of BioSil A by successive elution with (A) 100 ml CHCl3, (B) 100 ml of 1% (v/v) MeOH/CHCl3, (C) 100 ml of 2% MeOH/CHCl3, (D) 100 ml of 4% MeOH/CHCl3, (E) 100 ml of 8% MeOH/CHCl3, and (F) 100 ml of 12% MeOH/CHCl3. The appropriate column fractions were combined and concentrated to dryness on the rotary evaporator. The oily residue was then taken up in 10 ml of CH2Cl2, filtered from the small amount of insoluble material, and again concentrated to dryness. The residue was further dried under high vacuum to yield 168 mg (68%) of product as a colorless viscous oil.

후처리

  1. customThe crude reaction product
  2. customwas purified by chromatography on a 1.7×24 cm column of BioSil A by successive elution with (A) 100 ml CHCl3, (B) 100 ml of 1% (v/v) MeOH/CHCl3, (C) 100 ml of 2% MeOH/CHCl3, (D) 100 ml of 4% MeOH/CHCl3, (E) 100 ml of 8% MeOH/CHCl3, and (F) 100 ml of 12% MeOH/CHCl3
  3. concentrationconcentrated to dryness on the rotary evaporator
  4. filtrationfiltered from the small amount of insoluble material
  5. concentrationagain concentrated to dryness
  6. customThe residue was further dried under high vacuum

출처 및 근거

ORD 기록
ord-11734697bc8b4862a4a8b9e8de514a85
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416070

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