Diisopropylethylamine → HCID 58388237, compound

HRID 2047348Notes

Reaction equation

HRID 2047348 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([N:13]2[C@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:16][O:15][C:14]2=[O:25])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].CCN(C(C)C)C(C)C.CO[CH2:37][NH:38][C:39](=[O:48])[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([C:11](=[O:12])[N:13]2[C@H:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:16][O:15][C:14]2=[O:25])[CH2:37][NH:38][C:39](=[O:48])[O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11041660HCID 11041660, compoundHCID 58388236HCID 58388236, compound

Product 1

HCID 58388237HCID 58388237, compoundYield 17.49%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4R)-3-[3-(3,4-difluorophenyl)propanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one (1 g, 2.90 mmol) in dichloromethane (29.0 ml) at −60° C. was added TiCl4 (0.335 ml, 3.04 mmol) dropwise. After 30 min, DIPEA (0.556 ml, 3.19 mmol) was added and the solution stirred at 1 h at 0° C. phenylmethyl [(methyloxy)methyl]carbamate (1.131 g, 5.79 mmol)[prepared according to Barnett, C. J. et al, Tetrahedron Lett. 1997, 38, 5, 735.] was added and the reaction mixture stirred at 0° C. for 4 h. The solution was quenched with aqueous saturated ammonium chloride solution and extracted several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (0-50% EtOAc in hexanes) affording phenylmethyl {(2S)-2-[(3,4-difluorophenyl)methyl]-3-oxo-3-[(4R)-2-oxo-4-(phenylmethyl)-1,3-oxazolidin-3-yl]propyl}carbamate (548 mg, 0.506 mmol, 17.49% yield) as a clear oil:

Workup

  1. additionwas added
  2. customThe solution was quenched with aqueous saturated ammonium chloride solution
  3. extractionextracted several times with DCM
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-519c0e7b8ea641059d868fe6bb2f9a6d
Source dataset
uspto-grants-2013_11
Patent number
US08592475B2

Reaction notes

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