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

HRID 1396940ノート

反応式

HRID 1396940 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a54afd195dd4ab9ad35a00adf7aaa16
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

反応ノート

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