tert-Butyl carbamate → HCID 86691392, compound

HRID 540149Notes

Reaction equation

HRID 540149 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:22][C:16]=3[S:15](=[O:29])(=[O:28])[CH2:14][CH2:13]2)[CH:3]=1.[C:30](=[O:37])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[NH2:31].CC(C)([O-])C.[Na+]>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:27][CH2:26][CH2:25][CH2:24][O:23][C:21]1[CH:20]=[CH:19][C:17]2[CH2:18][N:12]([C:4]3[CH:3]=[C:2]([NH:31][C:30](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH2:13][CH2:14][S:15](=[O:29])(=[O:28])[C:16]=2[CH:22]=1

Participants

7

Reactant 3

HCID 77922tert-Butyl carbamateHCID 23676156Sodium t-butoxideHCID 71255500HCID 71255500, compound

Product 1

HCID 86691392HCID 86691392, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture solution of 3-{[4-(4-chloroquinolin-2-yl)-1,1-dioxido-2,3,4,5-tetrahydro-1,4-benzothiazepin-8-yl]oxy}propan-1-ol (300.0 mg, 0.70 mmol), tert-butyl carbamate (175.0 mg, 1.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (70.0 mg, 0.113 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (70.0 mg, 0.075 mmol) and sodium tert-butoxide (232.0 mg, 2.25 mmol) in 1,4-dioxane (2.0 mL) was heated with stirring at 120° C. for 2 hours under microwave irridiation. After being cooled to room temperature, the reaction mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 359.1 mg of the crude product as yellow oil which was used for next step without further purification. MS obsd. (ESI+) [(M+H)+] 514.

Workup

  1. temperatureAfter being cooled to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (50 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00f95200d76a4b4aaf57bff91bff8a6b
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

Loading…