HCID 66845777, compound → HCID 66846048, compound

HRID 386680Notes

Reaction equation

HRID 386680 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:27]=[CH:26][C:25]([NH:28]C(OC(C)(C)C)=O)=[CH:24][C:12]=3[C:13](=[O:23])[C:14]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][CH:4]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:12]=3[C:13](=[O:23])[C:14]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 66845777HCID 66845777, compound

Product 1

HCID 66846048HCID 66846048, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(6-methoxypyridin-3-yl)-3-benzyloxy-6-(N-tertbutoxycarbonylamino)-4H-1-benzopyran-4-one (0.067 mol) in DCM (90 ml) trifluoroacetic acid (30 ml) was added. The mixture was stirred for 1 hour at r.t. and concentrated. Aqueous NaHCO3 was added and the mixture was extracted with ethyl acetate, washed with water, dried, and concentrated. The solid was suspended in ethyl ether, filtered and dried. Yield: 78%; TLC (9/1 Chloroform/Methanol) Rf: 0.56.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additionAqueous NaHCO3 was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-508f6d2c620e4369b89e69d1270c8f97
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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