Acetic Acid → HCID 57495630、化合物

HRID 1092345ノート

反応式

HRID 1092345 の反応式
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][C:6]3([OH:14])[CH2:7][C:8]([OH:13])([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:15]([NH:22][C:23]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[C:18]([O:17][C:15](=[O:16])[NH:22][C:23]1([CH2:28][NH:2][CH:3]2[CH:10]3[CH2:9][C:8]4([OH:13])[CH2:7][C:6]([OH:14])([CH2:5][CH:4]2[CH2:12]4)[CH2:11]3)[CH2:24][CH2:25][CH2:26][CH2:27]1)([CH3:21])([CH3:19])[CH3:20]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamateHCID 57495631HCID 57495631、化合物

生成物 1

HCID 57495630HCID 57495630、化合物収率 56%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 5049666Sodium triacetoxyborohydride溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 6-amino-adamantane-1,3-diol hydrochloride (258 mg, J. Med. Chem. 50, 2007, 149), N-Boc-cycloleucinal (250 mg) and acetic acid (0.67 ml) in MeOH (5.0 ml), sodium triacetoxyborohydride was added at room temperature. The mixture was stirred at 60° C. for 30 min. The mixture was basified with saturated NaHCO3 solution. The mixture was extracted with AcOEt, washed with brine, dried over MgSO4 and evaporated. The residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1) to obtain the title compound (250 mg, 56%) as a white amorphous.

後処理

  1. additionwas added at room temperature
  2. extractionThe mixture was extracted with AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1)

出典と根拠

ORDレコード
ord-3f6498360f464d6caefacd9f6a365a9a
出典データセット
uspto-grants-2012_03
特許番号
US08129423B2

反応ノート

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