p-Toluenesulfonic acid → 6-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[2-(2-hydroxy-ethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

HRID 1096855ノート

反応式

HRID 1096855 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][C:12]([C:39]3[S:43][C:42]([O:44][CH2:45][CH2:46][O:47][Si](C(C)(C)C)(C)C)=[N:41][CH:40]=3)=[C:13]2[C:24](=[O:38])[N:25]([CH:35]2[CH2:37][CH2:36]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][C:12]([C:39]3[S:43][C:42]([O:44][CH2:45][CH2:46][OH:47])=[N:41][CH:40]=3)=[C:13]2[C:24](=[O:38])[N:25]([CH:35]2[CH2:37][CH2:36]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 685707807-{2-[2-(tert-Butyldimethylsilanyloxy)ethoxy]thiazol-5-yl}-6-[cyclo-propyl-(2,3-dichlorobenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

生成物 1

HCID 685713696-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[2-(2-hydroxy-ethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A sol. of compound E8 (0.37 mmol; 0.31 g) in MeOH (3.75 mL) was treated with para-toluenesulfonic acid (0.41 mmol; 78 mg), and the mixture was stirred at rt for 30 min. 10% aq. Na2CO3 (3.0 mL) was added and the solvents were partially removed under reduced pressure. The resulting suspension was extracted with EtOAc (25 mL), washed with 10% aq. Na2CO3 (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The product (0.26 g; 99%) was used for the next step without purification. LC-MS: tR=1.10 min; ES+: 709.41.

後処理

  1. customthe solvents were partially removed under reduced pressure
  2. extractionThe resulting suspension was extracted with EtOAc (25 mL)
  3. washwashed with 10% aq. Na2CO3 (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customThe product (0.26 g; 99%) was used for the next step without purification

出典と根拠

ORDレコード
ord-cdd9ba4bf93e4d7a988067e48db8f726
出典データセット
uspto-grants-2012_03
特許番号
US08138340B2

反応ノート

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