Pyridine → (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride

HRID 1396940노트

반응식

HRID 1396940 반응식
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14](O)=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].C(OC(NC[C@@H](CCCCC)C(O)=O)=O)C1C=CC=CC=1.N1C=CC=CC=1.[F:49]C1N=C(F)N=C(F)N=1>ClCCl>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([F:49])=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 66603339(2R)-[(benzyloxyformylamino)methyl]heptanoic acidHCID 86637307(R)-2-[(Benzyloxy-formyl-amino)-methyl]-heptanoic acid

생성물 1

HCID 86706374(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 250 mL round-bottomed flask was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoic acid (WO 2003101442, also named (2R)-[(benzyloxyformylamino)methyl]heptanoic acid) (4.40 g, 15 mmol) in dichloromethane (60 mL), followed by pyridine (1.453 mL, 18.00 mmol) and 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (2.168 g, 16.05 mmol). The reaction mixture was stirred at room temperature for 2 h, then was diluted with DCM, and washed with 5% Citric acid (150 mL) and sat. NaHCO3 (150 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography to provide (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride as a colorless oil (1.88 g, 42%). LCMS: (M+H)+: 296.0.

후처리

  1. washwashed with 5% Citric acid (150 mL) and sat. NaHCO3 (150 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-5a54afd195dd4ab9ad35a00adf7aaa16
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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