Sodium Hydroxide → HCID 131728264, compound

HRID 499698Notes

Reaction equation

HRID 499698 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:20])([CH3:19])[CH2:15][C:16](O)=[O:17])[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH3:38][O:39][C:40](=[O:52])[NH:41][CH:42]1[CH2:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][CH2:43]1.[OH-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:20])([CH3:19])[CH2:15][C:16]([N:44]2[C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:51][CH:42]([NH:41][C:40]([O:39][CH3:38])=[O:52])[CH2:43]2)=[O:17])[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 19697568Carbamic acid, (1,2,3,4-tetrahydro-3-quinolinyl)-, methyl ester, (-)-HCID 68653917HCID 68653917, compound

Product 1

HCID 131728264HCID 131728264, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
15 °C

Procedure

8.88 ml of triethylamine are added to a solution of 6.67 g of 4(S)-(3-carboxy-2,2-dimethyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester in 200 ml of methylene chloride under argon. The mixture is cooled to 15° C. and 5.54 g of bis(2-oxo-3-oxazolidinyl)phosphinic chloride are added. The mixture is stirred at room temperature for 2 hours. A solution of 4.36 g of (1,2,3,4-tetrahydro-quinolin-3(R,S)-yl)-carbamic acid methyl ester [177202-73-2] in 100 ml of methylene chloride is added, followed by addition of 2.11 g of 4-N,N-dimethylaminopyridine. The reaction mixture is stirred at room temperature for 17 hours. The mixture is poured into 1M NaOH and extracted with tert-butyl methyl ether (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a slightly yellow oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.39 (1:3 EtOAc-heptane); Rt=5.03 (gradient I).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 17 hours
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db055fe425dd4c6f87cab2b334f8cb1f
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

Loading…