HCID 18442425, compound → HCID 18442433, compound

HRID 458933Notes

Reaction equation

HRID 458933 reaction equation
[O:1]=[S:2]1(=[O:33])[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[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)[C:5](=O)[C:4]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[O:33]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[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]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3]1

Participants

4

Reactant 2

HCID 18442425HCID 18442425, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18442433HCID 18442433, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-methylthio-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 97; 0.41 g, 0.79 mmol) in anhydrous ether (15 ml) was added LiAlH4 (0.15 g, 3.97 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 2.5 hours. The reaction flask was cooled to 0° C. and the excess LiAlH4 was quenched by adding water (0.3 ml) and 2 M aqueous NaOH (0.3 ml). The mixture was filtered and the filtrate was dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM as eluent to give the title compound 0.265 g (68%). NMR (300 MHz) 0.8–0.90 (m, 6H), 1.0–1.47 (m, 12H), 2.33 (s, 3H), 3.17 (s, 2H), 3.70 (s, 2H), 3.93 (s, 3H), 7.03–7.08 (m, 3H), 7.23–7.32 (m, 3H); m/z 496.

Workup

  1. temperatureThe reaction flask was cooled to 0° C.
  2. customthe excess LiAlH4 was quenched
  3. additionby adding water (0.3 ml) and 2 M aqueous NaOH (0.3 ml)
  4. filtrationThe mixture was filtered
  5. customthe filtrate was dried
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e3171c000e88437d84b8a0ac0f5e75ed
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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