Water → HCID 18442432, compound

HRID 458934Notes

Reaction equation

HRID 458934 reaction equation
[O:1]=[S:2]1(=[O:32])[C:8]2[CH:9]=[C:10]([O:15]C)[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:5][C:4]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:3]1.B(Br)(Br)Br.O.O.NN>C(Cl)Cl>[O:32]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([OH:15])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:5][C:4]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 25134Boron tribromideHCID 18442433HCID 18442433, compound

Product 1

HCID 18442432HCID 18442432, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dioxo-3,3-dibutyl-5-(4-chlorophenyl)-7-methylthio-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 98; 0.26 g 0.52 mmol) in anhydrous DCM (10 ml) was added boron tribromide (2.63 g, 10.48 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 2.5 h. The reaction flask was cooled to 0° C., water (20 ml) and hydrazine monohydrate (0.5 ml) was added. The organic layer was separated, dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM/EtOAc (100:5 and 100:10) as eluent to give the title compound 0.20 g (80%). NMR (500 MHz) 0.85 (t, 6H), 1.03–1.28 (m, 8H), 1.35–1.46 (m, 4H), 2.39 (s, 3H), 3.21 (s, 2H), 3.73 (s, 2H), 7.04 (d, 2H), 7.29–7.34 (m, 3H), 7.44 (s, 1H); m/z 482.

Workup

  1. temperatureThe reaction flask was cooled to 0° C.
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-aaa3f4c7fb3f4690aaf96d9001d988c8
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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