Triethylamine → HCID 178431689, compound

HRID 339860Notes

Reaction equation

HRID 339860 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[C:20]([CH3:22])([CH3:21])[O:19][C:18]([NH:23][C@H:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[N:17][S:16]2(=[O:42])=[O:41])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C(N(CC)CC)C>CO.[Pd]>[Si:28]([O:27][CH2:26][CH2:25][C@H:24]([NH:23][C:18]1[O:19][C:20]([CH3:22])([CH3:21])[CH:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[S:16](=[O:42])(=[O:41])[N:17]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178431690HCID 178431690, compound

Product 1

HCID 178431689HCID 178431689, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Under inert gas, 1.03 g [5-(3-benzyloxyphenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine were initially charged in 20 ml of methanol and, with addition of 0.24 ml of triethylamine and 359 mg of 10% Pd/C, stirred under a hydrogen atmosphere for 3.75 hours. The completeness of the conversion was checked by LCMS, and the reaction was once again admixed with 359 mg of 10% Pd/C and stirred under a hydrogen atmosphere for a further 16 hours. According to LCMS, the detachment of the benzyl protecting group remained incomplete. After filtration to remove the solid residues, the filtrate was admixed again with 359 mg of 10% Pd/C. After stirring under a hydrogen atmosphere for 5 h, another 359 mg of 10% Pd/C were added and, after a further 2 hours, the reaction was found to be complete by checking with LCMS. After filtration to remove the catalyst residues, the filtrate was freed of the solvent under reduced pressure. This gave the product (764 mg) with a molecular weight of 518.8 g/mol (C26H38N2O5SSi); MS (ESI): m/e=519 (M+H+).

Workup

  1. stirringstirred under a hydrogen atmosphere for a further 16 hours
  2. filtrationAfter filtration
  3. customto remove the solid residues
  4. stirringAfter stirring under a hydrogen atmosphere for 5 h
  5. additionanother 359 mg of 10% Pd/C were added and, after a further 2 hours
  6. filtrationAfter filtration
  7. customto remove the catalyst residues

Sources & evidence

ORD record
ord-b91ba95084fa4f8a938926b19296a5f3
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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