Triethylamine → (4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-one

HRID 1246376

Reaction equation

HRID 1246376 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C@@H:10]([CH:25]([CH3:27])[CH3:26])[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[CH:25]([C@H:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][C:2](=[O:3])[NH:9]1)([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 854145(S)-(-)-2-Amino-3-methyl-1,1-diphenyl-1-butanol

Product 1

HCID 9838646(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-oneYield 86.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Trichloromethyl chloroformate (2.71 g, 13.7 mmol) was added to a mixture of (S)-2-amino-3-methyl-1,1-diphenyl-1-butanol (2) (3.18 g, 12.45 mmol) and triethylamine (2.68 g, 26.52 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 2 h at the same temperature and then poured into a brine solution (250 ml). The aqueous layer was made basic with NaOH pellets and organic products were extracted into AcOEt (5×200 ml). Combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The resulting crude product was washed with diethyl ether to obtain the title compound (3) (3.03 g, 86%) as a white solid. m.p. 250–251° C. (liti 250–251° C.). [α]D25=−201.59° (c, 0.0252 in DMSO). δH (DMSO-d6) 0.51 (3H, d, 3J=6.60 Hz, CH3), 0.92 (3H, d, 3J=7.20 Hz, CH3), 1.86 (1H, ds, 3J=2.10 and 6.60 Hz, CH—Me2), 4.46 (1H, d, 3J=6.5 Hz, CH—NH2), 7.24–7.72 (10H, m, Ar—H), 8.14 (1H, s, NH). δC 15.2 and 20.9 (CH3), 29.8 (CH), 64.9 (CH—NHCO), 88.4 (C—O), 125.8, 126.2, 127.9, 128.4, 128.8 and 129.1 (Ar), 140.5 and 146.1 (α-Ar), 158.1 (C═O). Ir 3295 (NH2), 1765 and 1745 (C═O). m/e (CI—NH3) 282 (MH+, 25%), 299 (MNH4+, 8%), 238 (96%), 223 (100%), 72 (100%).

Workup

  1. extractionwere extracted into AcOEt (5×200 ml)
  2. dry with materialCombined organic extracts were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-56149978dbb04527ba3483bc9c2c6d19
Source dataset
uspto-grants-2006_10
Patent number
US07126028B1

Linked notes

Loading…