Sodium hydride → HCID 178487628, compound

HRID 20663Notes

Reaction equation

HRID 20663 reaction equation
[H-].[Na+].[NH2:3][C@@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1.Cl[C:14]1[C:23]2[C:18](=[C:19]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[O:17][C:16](=[O:32])[CH:15]=1.OP([O-])(O)=O.[K+]>CS(C)=O>[CH:27]1([O:26][C:19]2[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[C:23]3[C:18]=2[O:17][C:16](=[O:32])[CH:15]=[C:14]3[NH:3][C@@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516951Monobasic potassium phosphateHCID 771747944-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-oneHCID 178511566HCID 178511566, compound

Product 1

HCID 178487628HCID 178487628, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (50 mg, 60%, 1.25 mmol) was added to a solution of cis-4-amino-1-cyclohexanecarboxylic acid (83 mg, 0.580 mmol) and anhydrous DMSO (2 mL) at rt under N2. After 10 min, 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (114 mg, 0.387 mmol, Example 7, Step 1) was added, and the mixture was stirred for 3 d, poured into 1M KH2PO4 and extracted with ethyl acetate. The extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (30→100% MeCN/H2O) to give cis-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)cyclohexanecarboxylic acid: 1H NMR (400 MHz, DMSO-d6): δ 7.85 (d, 1H), 7.10 (d, 1H), 7.01 (d, 1H), 5.10 (s, 1H), 4.81 (m, 1H), 3.87 (s, 3H), 3.50 (m, 1H), 2.56 (m, 1H), 2.04 (m, 2H), 1.79-1.58 (m, 14H); MS (ESI): 402.0.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (30→100% MeCN/H2O)

Sources & evidence

ORD record
ord-d00af014a3574eae896426b144fefafb
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

Loading…