HCID 11101284、化合物 → 3-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

HRID 1033397ノート

反応式

HRID 1033397 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16][CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+]>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16](=[O:29])[CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 11101284HCID 11101284、化合物HCID 23667635Sodium periodate

生成物 1

HCID 186514853-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

A solution of 179 mg (0.46 mmol) of 3-t-butoxycarbonylamino-3-methyl-N-[3,4-dihydro-4-oxo-1,5-benzothiazepin-3(S)-yl]-butanamide (Example 46, Step A) in 4.5 mL of methanol/water (5:1) was treated with 102 mg (0.48 mmol, 1.05 eq) of sodium periodate and stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was redissolved in chloroform, dried over potassium carbonate, filtered and concentrated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A in addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was redissolved in chloroform
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash chromatography on silica
  8. washeluting with ethyl acetate
  9. customafforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A
  10. additionin addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B

出典と根拠

ORDレコード
ord-b65511f30d2f424d9c6f4317646800a3
出典データセット
uspto-grants-1994_05
特許番号
US05310737

反応ノート

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