Isopropyl Acetate → HCID 86598223, compound

HRID 748636Notes

Reaction equation

HRID 748636 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH2:13])=[CH:6][CH:5]=1.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:35]Br)=[CH:30][C:29]=1[NH:45][CH:46]=[O:47])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)C)(=O)C>O.CS(C)=O>[NH2:13][C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][CH2:35][C@@H:34]([C:31]2[CH:32]=[CH:33][C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:29]([NH:45][CH:46]=[O:47])[CH:30]=2)[O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7915Isopropyl AcetateHCID 11430Potassium CarbonateHCID 15606252HCID 15606252, compoundHCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethane

Product 1

HCID 86598223HCID 86598223, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen, (R)-N2-[4-(2-aminoethyl)phenyl]-1-phenylethane-1,2-diamine (Example 5) (22.4 g, 1.4 equiv), N-[2-benzyloxy-5-((R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl)phenyl]formamide (29.2 g, 1.0 equiv), potassium carbonate (34.7 g, 4.0 equiv) were combined with dimethyl sulfoxide (35 mL). The resulting slurry was stirred at 100° C. for 85 minutes. The mixture was cooled to room temperature and water (200 mL) and isopropyl acetate (200 mL) were added. The layers were separated and the organic layer was washed with water (200 mL) followed by aqueous saturated sodium chloride (150 mL) and dried over anhydrous magnesium sulfate (20 g). The solids were removed by filtration and the filtrate concentrated to yield crude title intermediate as an amber colored oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with water (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate (20 g)
  5. customThe solids were removed by filtration
  6. concentrationthe filtrate concentrated
  7. customto yield crude title intermediate as an amber colored oil

Sources & evidence

ORD record
ord-78b01d4f96e84e4d84561491168ed6fd
Source dataset
uspto-grants-2008_07
Patent number
US07399863B2

Reaction notes

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