Trifluoroacetic acid → HCID 67642579, 화합물

HRID 1597764노트

반응식

HRID 1597764 반응식
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6](=[O:28])[CH:7]([OH:27])[CH:8]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(F)(F)C(O)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6](=[O:28])[C:7](=[O:27])[CH:8]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 67641967HCID 67641967, 화합물

생성물 1

HCID 67642579HCID 67642579, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 4-hydroxy-6-phenyl-5-[((phenylmethoxy)carbonyl)amino]-3-oxohexanoic acid ethyl ester (397 mg, 1.0 mmol) is dissolved in acetonitrile (15 ml) and the Dess-Martin periodinane (1.27 g, 3.0 mmol)) is added. To the mixture trifluoroacetic acid (342 mg, 3.0 mmol) is added and the mixture is stirred for 48 h. The solvent is removed in vacuo and EtOAc (100 ml) is added, followed by the addition of a solution of NaHCO3 (0.80 g) and Na2S2O3 (1.41 g) in H2O (25 ml). The organic layer is separated and the aqueous phase extracted with ethyl acetate. The combined extracts are dried over Na2S2O3 and the solvent is removed in vacuo. The product is purified by flash chromatography on silica gel.

후처리

  1. customThe solvent is removed in vacuo and EtOAc (100 ml)
  2. additionis added
  3. additionfollowed by the addition of a solution of NaHCO3 (0.80 g) and Na2S2O3 (1.41 g) in H2O (25 ml)
  4. customThe organic layer is separated
  5. extractionthe aqueous phase extracted with ethyl acetate
  6. dry with materialThe combined extracts are dried over Na2S2O3
  7. customthe solvent is removed in vacuo
  8. customThe product is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-37af870ddf6447d395fe4de0c828791b
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736520

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