Sulfuric Acid → HCID 18442428, compound

HRID 458939Notes

Reaction equation

HRID 458939 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O.[O:12]=[S:13]1(=[O:44])[C:19]2[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=2[N:17]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)[C:16](=O)[C:15]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:14]1>C1COCC1>[O:44]=[S:13]1(=[O:12])[C:19]2[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=2[N:17]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:16][C:15]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:14]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 18442426HCID 18442426, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18442428HCID 18442428, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To LiAlH4 (5.76 g, 151 mmol) were added THF (200 ml). The reaction mixture was cooled to 0° C. and H2SO4 (4.06 ml, 76 mmol) were added slowly with a syringe. After the addition was completed the reaction was stirred for 10 minutes, Then 1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-nitrophenyl)-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 104; 2.57 g, 5.06 mmol) dissolved in THF (50 ml) was added at 0° C. After vigorous stirring for 1 hour the cooling bath was removed and the reaction was heated to 40° C. overnight. Then Na2SO4.10H2O (3–4 teaspoons), water (8 ml), NaOH (15%, aq) (8 ml), water (25 ml) and MeOH (30 ml) were added in that order. The precipitate was removed by filtration and rinsed with DCM/MeOH. The solvent was dried, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography using DCM:EtOAc, 9:1 then 3:1 as eluent to give the title compound 0.6 g (27%). M/z 431.3.

Workup

  1. additionAfter the addition
  2. additionwas added at 0° C
  3. stirringAfter vigorous stirring for 1 hour the cooling bath
  4. customwas removed
  5. temperaturethe reaction was heated to 40° C. overnight
  6. additionThen Na2SO4.10H2O (3–4 teaspoons), water (8 ml), NaOH (15%, aq) (8 ml), water (25 ml) and MeOH (30 ml) were added in that order
  7. customThe precipitate was removed by filtration
  8. washrinsed with DCM/MeOH
  9. customThe solvent was dried
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b97a8ca9fdfd4cdb816d6689dc3f183d
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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