Sodium Bicarbonate → (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

HRID 1604749Notes

Reaction equation

HRID 1604749 reaction equation
[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][N:14]2[C@H:23]([C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][C@H:21]3[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15]2)[O:11]C(=O)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC(S([O-])(=O)=O)=CC=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:9][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:12]([OH:11])[CH2:13][N:14]1[C@H:23]([C:24]([NH:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][C@H:21]2[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86753580(3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-yl methyl]-N-tert.-butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonate

Product 1

HCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

34.7 g of (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo -oxazolidin-5-yl methyl]-N-tert.-butyl-decahydro -isoquinoline-3-carboxamide-p-nitrobenzenesulphonate were divided between 110 ml of ethyl acetate and 110 ml of saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate and the ethyl acetate extracts washed with 110 ml of saturated sodium bicarbonate and with water. The organic extracts were evaporated and the residue diluted with 55 ml of ethanol and combined with stirring with a solution of 11.0 g of sodium hydroxide in 55 ml of water. The mixture was refluxed for 5 hours, diluted with 55 ml of water and cooled to room temperature. The suspension was filtered and the residue washed with water until the filtrate was neutral. The residue was evaporated and yielded 20.7 g (93%) 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert. -butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide, melting point 175-176°.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe ethyl acetate extracts washed with 110 ml of saturated sodium bicarbonate and with water
  3. customThe organic extracts were evaporated
  4. additionthe residue diluted with 55 ml of ethanol
  5. temperatureThe mixture was refluxed for 5 hours
  6. additiondiluted with 55 ml of water
  7. filtrationThe suspension was filtered
  8. washthe residue washed with water until the filtrate
  9. customThe residue was evaporated

Sources & evidence

ORD record
ord-43012ef865e2452f8f216dd9c0e82847
Source dataset
uspto-grants-1999_11
Patent number
US05994555

Reaction notes

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