Veratroyl chloride → HCID 18638173, compound

HRID 1165768Notes

Reaction equation

HRID 1165768 reaction equation
[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3]1=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=3.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:36](Cl)=[O:37]>N1C=CC=CC=1.C(Cl)Cl>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:36]([O:1][C@@H:2]1[C@H:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3]1=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:37]

Participants

5

Reactant 2

HCID 77070Veratroyl chlorideHCID 13823438HCID 13823438, compound

Product 1

HCID 18638173HCID 18638173, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 g (0.0047 mol) of (-)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[ 1,2-b][1,4]thiazepin-4(5H)-one in 25 ml of dry pyridine was added dropwise 1.6 g (0.0082 mol) of 3,4-dimethoxybenzoyl chloride at ice-bath temperature. After the addition, the reaction mixture was kept at ice-bath temperatures for 17 hours and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and cold 10% potassium carbonate. The combined ethyl acetate solutions were washed with brine, dried (MgSO4) and the solvent was removed to give 3.3 g of crude product, which was dissolved in methylene chloride and chromatographed using 45 g of silica gel. The comumn was eluted with 50 ml portions of methylene chloride-acetone (80:20). Fractions 21-50 were collected and the solvent was removed to give 2.5 g (92%) of (-)-cis-2,3-dihydro-3-[(3,4-dimethoxybenzoyl)oxy]-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b][1,4]thiazepin-4(5H)-one as an amorphous solid, [α]D25 + 47.39° (C 0.928, MeOH).

Workup

  1. additionAfter the addition
  2. customthe reaction mixture was kept at ice-bath
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and cold 10% potassium carbonate
  5. washThe combined ethyl acetate solutions were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed
  8. customto give 3.3 g of crude product, which
  9. customchromatographed
  10. washThe comumn was eluted with 50 ml portions of methylene chloride-acetone (80:20)
  11. customFractions 21-50 were collected
  12. customthe solvent was removed

Sources & evidence

ORD record
ord-8b528a054a7b431f8937fd91e977cdd0
Source dataset
uspto-grants-1990_03
Patent number
US04912102

Reaction notes

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