1,2-Dichloroethane → HCID 86585259, 화합물

HRID 1007723노트

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HRID 1007723 반응식
C([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([I:18])[CH:12]=1)(OC(C)(C)C)=O.[C:22](OC(=O)C)(=[O:24])C.[CH2:29](Cl)[CH2:30]Cl.C1C=CC2N([OH:42])N=NC=2C=1.[NH3:43].C(O)(=O)[CH2:45][C:46]([CH2:51]C(O)=O)([C:48](O)=O)[OH:47]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.CC(O)C>[C:22]([NH:43][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:29](=[O:42])[CH3:30])=[C:13]([I:18])[CH:12]=1)[NH2:8])([O:47][C:46]([CH3:45])([CH3:48])[CH3:51])=[O:24]

참가 물질

10

반응물 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 311Citric AcidHCID 7918Acetic AnhydrideHCID 757711-HydroxybenzotriazoleHCID 15545208N-(tert-Butoxycarbonyl)-3-iodo-L-tyrosine

생성물 1

HCID 86585259HCID 86585259, 화합물

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 3776Isopropanol용매

실험 절차

To a solution of N-Boc-3-iodotyrosine (0.380 g, 0.93 mmol) in pyridine (1 mL) were added acetic anhydride (105 μL, 1.1 mmol) and DMAP (10 mg, cat). The solution was stirred 1.5 h then diluted in 5% citric acid (20 mL), and the product extracted with EtOAc. The organic solution was evaporated and the residue dissolved in MeCN (4 mL). To the stirred cold (ice bath) solution were added EDC (0.196 g, 1.0 mmol) and HOBt (0.135 g, 1.0 mmol). After stirring for 1 h, a 2 N solution of ammonia in iPrOH (3 mL) was added. The suspension was stirred 1 h at 5° C., the solid was filtered, the filtrate evaporated and the residue purified by flash chromatography (gradient 3-5% MeOH/chloroform) to yield N-Boc-O-acety-3-iodotyrosine amide.

후처리

  1. extractionthe product extracted with EtOAc
  2. customThe organic solution was evaporated
  3. dissolutionthe residue dissolved in MeCN (4 mL)
  4. stirringAfter stirring for 1 h
  5. stirringThe suspension was stirred 1 h at 5° C.
  6. filtrationthe solid was filtered
  7. customthe filtrate evaporated
  8. customthe residue purified by flash chromatography (gradient 3-5% MeOH/chloroform)

출처 및 근거

ORD 기록
ord-0227350579d345fb90220001abbee975
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794404B2

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