Triethylamine → tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

HRID 507831Notes

Reaction equation

HRID 507831 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.C(N(CC)CC)C.[NH2:23][CH2:24][C@H:25]([CH:42]([CH3:44])[CH3:43])[CH2:26][C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[OH-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH:23][CH2:24][C@H:25]([CH:42]([CH3:44])[CH3:43])[CH2:26][C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 176069102-(3-Methoxypropoxy)benzoic acidHCID 68623939tert-butyl 4(S)-(2(S)-aminomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

Product 1

HCID 68624344tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The solution of 2.99 g of 2-(3-methoxypropoxy)benzoic acid [179992-98-4] and 3.95 ml of triethylamine in 60 ml of dichloromethane is cooled to 15° C. and admixed with 3.70 g of bis-(2-oxo-3-oxazolidynyl)phosphinoyl chloride. The mixture is stirred over 1 hour and subsequently admixed with the solution of 2.22 g of tert-butyl 4(S)-(2(S)-aminomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate in 3 ml of dichloromethane and 0.703 g of 4-dimethylaminopyridine, and stirred overnight. The reaction mixture is poured onto 1M NaOH and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.29 (1:1 EtOAc-heptane); Rt=5.49 (gradient I).

Workup

  1. stirringstirred overnight
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9eb4e79809184ddc90686a7e7421ffff
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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