Carbon Dioxide → HCID 22459178, compound

HRID 2184989Notes

Reaction equation

HRID 2184989 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([N-]C(C)C)(C)C.[Li+].C(=O)=O.COC1C2OC3C(=CC=CC=3)C(C(O)=O)C=2C=CC=1.C(Cl)(=O)[C:48]([Cl:50])=[O:49]>O1CCCC1.C1(C)C=CC=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]([C:48]([Cl:50])=[O:49])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 65578Oxalyl chlorideHCID 2724682Lithium diisopropylamideHCID 125543394-Methoxy-9H-xantheneHCID 22459180HCID 22459180, compound

Product 1

HCID 22459178HCID 22459178, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

(RS)-4-Methoxy-9H-xanthene-9-carbonyl chloride was prepared according to general methods described in WO 9706178. 4-Methoxy-xanthene [J.Med.Chem., 32(10), 2357(1989)] was deprotonated with lithium diisopropylamide in tetrahydrofuran followed by treatment with carbon dioxide. The resulting (RS)-4-methoxy-9H-xanthene-9-carboxylic acid (white solid and MS: m/e=256.0 (M+)) was chlorinated with oxalyl chloride in toluene/DMF and yielded after evaporation of the reagent and solvents, the crude acid chloride, which was directly used without further purification.

Workup

  1. customyielded
  2. customafter evaporation of the reagent and solvents
  3. customthe crude acid chloride, which was directly used without further purification

Sources & evidence

ORD record
ord-cf85ecd894d449fa84316210d753f08b
Source dataset
uspto-grants-2002_06
Patent number
US06399641B1

Reaction notes

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