Dimethyl Sulfoxide → HCID 11742180, compound

HRID 358775Notes

Reaction equation

HRID 358775 reaction equation
CS(C)=O.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[CH2:14][CH:13]1[CH2:32][OH:33])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C(Cl)Cl>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[CH2:14][CH:13]1[CH:32]=[O:33])=[O:11])([CH3:7])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 10341501HCID 10341501, compound

Product 1

HCID 11742180HCID 11742180, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

methylene chloride (50 ml) is added dropwise at -78° C. a solution of dimethyl sulfoxide (2.86 g) in methylene chloride (20 ml). The mixture is stirred for 10 minutes. To the resulting reaction mixture is added dropwise a solution of 1-tertbutoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-methanol (5.0 g) obtained in Reference Example 4 in methylene chloride (10 ml). The mixture is stirred for 20 minutes. To the mixture is added triethylamine (7.4 g), followed by raising the reaction temperature up to room temperature. The reaction mixture is poured into ice water, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is recrystallized from ethyl acetate to give 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-carbaldehyde as colorless prisms (4.1 g), m.p. 160-161° C.

Workup

  1. customTo the resulting reaction mixture
  2. stirringThe mixture is stirred for 20 minutes
  3. extractionfollowed by extraction with methylene chloride
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c2b610457cd42f6a8361c5e9e69c20a
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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