m-Chloroperbenzoic acid → 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-1-(2-phenylethyl)-8H-pyrido[4',3':4,5]thieno[2,3-e]-1,4-diazepine-2-one

HRID 1836203Notes

Reaction equation

HRID 1836203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:26]3[CH2:27][CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][C:25]=3[S:24][C:10]=2[N:11]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12](=[O:15])[CH2:13][N:14]=1.ClC1C=C(C=CC=1)C(OO)=[O:43].C(OC(C)C)(C)C.CCC(C)C>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:26]3[CH2:27][CH2:28][NH:29][CH2:30][C:25]=3[S:24][C:10]=2[N:11]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12](=[O:15])[CH:13]([OH:43])[N:14]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23498626t-butyl 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-2-oxo-1-(2-phenylethyl)-8H-pyrido[4',3':4.5]thieno[2,3-e]-1,4-diazepine-8-carboxylateHCID 86591840Isopropyl ether isopentane

Product 1

HCID 158879725-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-1-(2-phenylethyl)-8H-pyrido[4',3':4,5]thieno[2,3-e]-1,4-diazepine-2-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

t-butyl 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-2-oxo-1-(2-phenylethyl)-8H-pyrido[4′,3′:4.5]thieno[2,3-e]-1,4-diazepine-8-carboxylate (22 g, 41 mmol) is dissolved a 23° C. in 1,2-chloro ethane (320 ml). Meta-chloroperoxybenzoic acid at 85% (21.6 g, 0.1 mol) is added. Agitation is carried out for 24 hours at 23° C. then a solution of 5N sodium hydroxide (400 ml) is added. After decanting, the organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated with a rotary evaporator. After purification by chromatography on a silica column (eluent: ethyl acetate-heptane: 50-50 to 80-20), the fractions containing only the product ae evaporated. The solid obtained is agitated in a mixture of solvents: isopropyl ether-isopentane (20-80). After filtration on frit and washing with isopentane, the desired product is obtained in the form of a white powder (5.9 g, 26%).

Workup

  1. customAfter decanting
  2. washthe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated with a rotary evaporator
  6. customAfter purification by chromatography on a silica column (eluent: ethyl acetate-heptane: 50-50 to 80-20)
  7. additionthe fractions containing only the product ae
  8. customevaporated
  9. customThe solid obtained
  10. filtrationAfter filtration on frit
  11. washwashing with isopentane

Sources & evidence

ORD record
ord-b10408599cda4202b913c3bae5fca6c0
Source dataset
uspto-grants-2004_08
Patent number
US06777408B1

Reaction notes

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