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

HRID 1096854ノート

反応式

HRID 1096854 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:40]3[S:44][C:43]([O:45][CH2:46][CH2:47][O:48][Si](C(C)(C)C)(C)C)=[N:42][CH:41]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:38][CH2:37]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[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]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH:10]([CH2:11][C:12]([C:40]3[S:44][C:43]([O:45][CH2:46][CH2:47][OH:48])=[N:42][CH:41]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:37][CH2:38]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[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 685705317-{2-[2-(tert-Butyldimethylsilanyloxy)ethoxy]thiazol-5-yl}-6-[cyclo-propyl-(3-methoxy-2-methylbenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

生成物 1

HCID 685707976-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[2-(2-hydroxyethoxy)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 E7 (3.55 mmol; 2.84 g) in MeOH (35.5 mL) was treated with para-toluenesulfonic acid (3.91 mmol; 0.74 g), and the mixture was stirred at rt for 30 min. 10% aq. Na2CO3 (20 mL) was added, and the solvents were partially removed under reduced pressure. The resulting suspension was extracted with EtOAc (200 mL), washed with 10% aq. Na2CO3 (100 mL), sat. aq. NaHCO3 (100 mL), and brine (100 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The product (2.46 g; 99%) was used for the next step without purification. LC-MS: tR=1.07 min; ES+: 685.50.

後処理

  1. customthe solvents were partially removed under reduced pressure
  2. extractionThe resulting suspension was extracted with EtOAc (200 mL)
  3. washwashed with 10% aq. Na2CO3 (100 mL), sat. aq. NaHCO3 (100 mL), and brine (100 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customThe product (2.46 g; 99%) was used for the next step without purification

出典と根拠

ORDレコード
ord-ffdb970482e5475aa1856b519fd08a29
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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