Formaldehyde → HCID 59261073, compound

HRID 643546Notes

Reaction equation

HRID 643546 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][C:7]([CH:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=2[OH:24])=[O:11])[CH2:6]1)(=[O:3])[CH3:2].C=O.S(O)([C:36]1C=CC(C)=CC=1)(=O)=O.O>C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]1[CH2:9][CH2:8][C:7]([CH:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])([C:10]([N:12]2[CH2:13][C:14]3[CH:19]=[C:18]([C:20]([F:22])([F:21])[F:23])[CH:17]=[CH:16][C:15]=3[O:24][CH2:36]2)=[O:11])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 59261064HCID 59261064, compound

Product 1

HCID 59261073HCID 59261073, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[1-(Acetyloxy)ethyl]-3-({[2-hydroxy-5-(trifluoromethyl)benzyl]amino}carbonyl)cyclopentyl acetate was combined with paraformaldehyde (ca. 6 g) and TsOH H2O (ca. 100 mg) in 130 mL of toluene. The flask was equipped with a Dean Stark trap and condenser and the reaction mixture was stirred at reflux for 1.5 h. The reaction mixture was filtered to remove remaining paraformaldehyde and the filtrate was concentrated. Purification of the resulting residue was accomplished by MPLC (silica, 65% ethyl acetate/hexanes) to afford 3-[1-(acetyloxy)ethyl]-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentyl acetate as a mixture of 8 diasteomers.

Workup

  1. customThe flask was equipped with a Dean Stark trap and condenser
  2. temperatureat reflux for 1.5 h
  3. filtrationThe reaction mixture was filtered
  4. customto remove
  5. concentrationthe filtrate was concentrated
  6. customPurification of the resulting residue

Sources & evidence

ORD record
ord-92b848cd52d94257a6abed7e64e57fef
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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