HCID 11101284, compound → 3-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

HRID 1033397Notes

Reaction equation

HRID 1033397 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16][CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+]>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16](=[O:29])[CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11101284HCID 11101284, compoundHCID 23667635Sodium periodate

Product 1

HCID 186514853-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 179 mg (0.46 mmol) of 3-t-butoxycarbonylamino-3-methyl-N-[3,4-dihydro-4-oxo-1,5-benzothiazepin-3(S)-yl]-butanamide (Example 46, Step A) in 4.5 mL of methanol/water (5:1) was treated with 102 mg (0.48 mmol, 1.05 eq) of sodium periodate and stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was redissolved in chloroform, dried over potassium carbonate, filtered and concentrated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A in addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was redissolved in chloroform
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash chromatography on silica
  8. washeluting with ethyl acetate
  9. customafforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A
  10. additionin addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B

Sources & evidence

ORD record
ord-b65511f30d2f424d9c6f4317646800a3
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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