Potassium cyanate → (2R)-2-[(2R)-4-[4-(carbamoylamino)phenyl]-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamide

HRID 876573Notes

Reaction equation

HRID 876573 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([C@@H:14]([OH:26])[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[O:16])[C:9]2=[O:27])=[CH:4][CH:3]=1.[O-:28][C:29]#[N:30].[K+]>C(O)(C)=O.O.O>[C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([C@@H:14]([OH:26])[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[O:16])[C:9]2=[O:27])=[CH:4][CH:3]=1)(=[O:28])[NH2:30]

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 67032877(2R)-2-[(2R)-4-(4-aminophenyl)-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamide

Product 1

HCID 67223031(2R)-2-[(2R)-4-[4-(carbamoylamino)phenyl]-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamideYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of compound 26-5 (70 mg) in AcOH—H2O (6 mL-2 mL), was added a solution of potassium cyanate (KOCN; 31 mg) in water (2 mL). The reaction mixture was stirred at 40-50° C. for 3 hours and at room temperature overnight to precipitate. The resulting precipitate was collected by filtration, rinsed with waster and dried in vacuo to obtain compound 27-1 (70 mg) as a colorless amorphous solid.

Workup

  1. customto precipitate
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with waster
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7848b6ddedf045a5b7bd6554cde0b8dc
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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