Sodium Carbonate → (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonate

HRID 2209746Notes

Reaction equation

HRID 2209746 reaction equation
[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[O:11][C:10](=[O:27])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([NH:32][C:33]([C@@H:35]1[CH2:44][C@H:43]2[C@H:38]([CH2:39][CH2:40][CH2:41][CH2:42]2)[CH2:37][NH:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C.Cl>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([S:15]([OH:17])(=[O:14])=[O:16])=[CH:23][CH:22]=1)([O-:26])=[O:25].[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][N:36]2[C@H:35]([C:33]([NH:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:44][C@H:43]3[C@H:38]([CH2:39][CH2:40][CH2:41][CH2:42]3)[CH2:37]2)[O:11][C:10](=[O:27])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 454736(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamideHCID 11058277[(4S,5S)-4-benzyl-2-oxo-5-oxazolidinyl]methyl 4-nitrobenzenesulfonate

Product 1

HCID 86749025(3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonateYield 88.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of 24.69 g of p-nitrobenzenesulphonic acid (4S, 5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester (Example 12), 15.0 g of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide and 10.0 g of sodium carbonate in 76 ml of 4-methyl-2-pentanone is heated under reflux for 10 hours while stirring. The suspension is cooled to 80° C., diluted with 176 ml of 4-methyl-2-pentanone and 54 ml of 3N hydrochloric acid, cooled to 40° C. and filtered. The residue is washed with water and 4-methyl-2-pentanone and dried to give 35.1 g (88%) of (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonate, [α]D20 =-31.2° (1% in DMF).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 10 hours
  3. temperaturecooled to 40° C.
  4. filtrationfiltered
  5. washThe residue is washed with water and 4-methyl-2-pentanone
  6. customdried

Sources & evidence

ORD record
ord-1f02c3cc5254452392a206d6d2bab84b
Source dataset
uspto-grants-1995_10
Patent number
US05455353

Reaction notes

Loading…