Citric Acid → HCID 66870865、化合物

HRID 402197ノート

反応式

HRID 402197 の反応式
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35][C:36]3[C:45]4[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=4)[N:39]=[C:38]([C:49]4[S:50][CH:51]=[C:52]([CH:54]([CH3:56])[CH3:55])[N:53]=4)[CH:37]=3)[CH2:12]1)[C:8](=[O:57])[NH:7]2)=[O:5])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH:54]([C:52]1[N:53]=[C:49]([C:38]2[CH:37]=[C:36]([O:35][CH:11]3[CH2:10][CH:9]4[N:13]([C:14](=[O:34])[N:15]([CH2:25][C:26]5[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=5)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:57])[CH2:24]5)[CH2:12]3)[C:45]3[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=3)[N:39]=2)[S:50][CH:51]=1)([CH3:56])[CH3:55]

参加物

5

反応物 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 66870831HCID 66870831、化合物

生成物 1

HCID 66870865HCID 66870865、化合物収率 60%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

Ethyl ester 137 (366 mg, 0.460 mmol) was dissolved in THF/MeOH/H2O 2:1:1 (30 mL) and 1M LiOH (4.6 mL, 4.40 mmol) was added dropwise at room temperature during 5 minutes after which the solution was stirred overnight. The mixture was acidified to pH 3-4 by addition of solid citric acid and the organic solvents were evaporated. The water phase was diluted with brine (50 mL) and was then extracted trice with DCM. The combined organic phase was washed twice with brine and was thereafter dried, filtered and concentrated. The crude was then purified by flash column chromatography (ethyl actetate/methanol 7:1) to give the title compound (212 mg, 60%). (M+H)+ calcd: 768.3. found: 768.7.

後処理

  1. customthe organic solvents were evaporated
  2. additionThe water phase was diluted with brine (50 mL)
  3. extractionwas then extracted trice with DCM
  4. washThe combined organic phase was washed twice with brine
  5. customwas thereafter dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified by flash column chromatography (ethyl actetate/methanol 7:1)

出典と根拠

ORDレコード
ord-4b6bbfafbc304de7a4817ad5406ffaef
出典データセット
uspto-grants-2014_06
特許番号
US08741926B2

反応ノート

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