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 1096854Notes

Reaction equation

HRID 1096854 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: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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ffdb970482e5475aa1856b519fd08a29
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

Loading…