Methanesulfonyl chloride → HCID 10861453、化合物

HRID 399514ノート

反応式

HRID 399514 の反応式
[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@@H:10]([O:12][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

生成物 1

HCID 10861453HCID 10861453、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline tert-butyl ester (573 mg, 1.99 mmol) in pyridine (3.5 mL) cooled to 0° C. was added methanesulfonyl chloride (0.31 mL, 3.99 mmol). The reaction mixture was stirred for 2 hours at ice temperature, diluted with ethyl acetate (30 mL), washed with 1M sodium hydrogencarbonate solution, 1M citric acid, water, dried (Na2SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 1% methanol/dichloromethane; yield 686 mg (94%). 400 MHz 1H NMR (CDCl3): δ1.42-1.44 (2s, 18H); 2.20 (m, 1H); 2.60 (m, 1H); 3.02 (s, 3H); 3.68-3.86 (m, 2H); 4.29 (m, 1H); 5.22 (m, 1H).

後処理

  1. washwashed with 1M sodium hydrogencarbonate solution, 1M citric acid, water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by flash silica gel chromatography
  5. washeluting with 1% methanol/dichloromethane

出典と根拠

ORDレコード
ord-3e7049f39c0d4db8bbce345cdc0ee0e8
出典データセット
uspto-grants-1998_10
特許番号
US05821261

反応ノート

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