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 1096855Notes

Reaction equation

HRID 1096855 reaction equation
[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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cdd9ba4bf93e4d7a988067e48db8f726
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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