Triethylamine → (4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-one

HRID 1246378Notes

Reaction equation

HRID 1246378 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C@@H:10]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[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.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cl-].[Na+].O>[CH2:25]([C@H:10]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:12][C:2](=[O:3])[NH:9]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 11430Potassium CarbonateHCID 7023048(2S)-2-Amino-1,1,3-triphenylpropan-1-ol

Product 1

HCID 9818858(4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-oneYield 97.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Trichloromethyl chloroformate (718 mg, 3.63 mmol) was added to a mixture of (S)-2-amino-1,1,3-triphenyl-1-propanol (6) (1.00 g, 3.30 mmol) and triethylamine (710 mg, 7.02 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 5 h at the same temperature and then poured into a brine solution (150 ml). The aqueous layer was made basic with powdered K2CO3 and organics were extracted into dichloromethane (3×50 ml). The combined organic extracts were dried over MgSO4/K2CO3 and concentrated under reduced pressure. The resulting crude product was washed with diethyl ether to obtain the title compound (7) (1.06 g, 97%) as a white solid. m.p. 259–261° C. (lit ? ° C.). [α]D25=−241.94° (c, 0.0211 in DMSO), δH (DMSO-d6) 2.18 (1H, dd, 3J=10.8 Hz, 2J=13.8 Hz, CH2—Ph), 2.52 (1H, dd, 3J=3.6 Hz, 2J=13.8 Hz, CH2—Ph), 4.67 (1H, dd, 3J=3.6 Hz, 3J=10.8 Hz, CH—NH2), 6.90–7.60 (15H, m, Ar—H). δC 44.2 (CH2—Ph), 50.5 (CH—NH), 94.1 (C—O), 130.5, 130.9, 131.5, 132.6, 132.8, 133.0, 133.1, 133.3 and 133.4 (o-, m- and p-Ar), 141.1, 143.4 and 146.5 (α-Ar), 163.7 (C═O), ir 3248 (NH2), 1760 and 1725 (C═O). m/e (CI—NH3) 330 (MH+, 5%), 347 (MNH4+, 6%), 196 (100%).

Workup

  1. extractionorganics were extracted into dichloromethane (3×50 ml)
  2. dry with materialThe combined organic extracts were dried over MgSO4/K2CO3
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-6e29ea218fe04cccab1558caefce8e75
Source dataset
uspto-grants-2006_10
Patent number
US07126028B1

Reaction notes

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