Triethylamine → HCID 66870053, compound

HRID 1422658Notes

Reaction equation

HRID 1422658 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][CH2:12][CH2:13][C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:19])[CH2:15][C:16]([CH3:18])=[CH2:17])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[CH2:12][CH2:13][C:14]([CH2:15][C:16]([CH3:18])=[CH2:17])([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:19][C:34]2=[O:36])([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 66869761HCID 66869761, compound

Product 1

HCID 66870053HCID 66870053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-(4-bromophenyl)propan-2-ylamino)-5-methyl-3-phenylhex-5-en-3-ol (60 mg, 149.3 μmol) in CH2Cl2 (15 mL) was added Et3N (75.5 mg, 746.3 μmol). The mixture was cooled to 0° C. and triphosgene (44.3 mg, 149.3 μmol) was added under nitrogen. The solution was stirred at 0° C. for 1 h. The reaction was quenched with water (15 mL) and extracted with CH2Cl2 (15 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrate under vacuum. The residue was purified by preparative TLC (petroleum ether: EtOAc =3:1) followed by preparative HPLC to afford 3-(2-(4-bromophenyl)propan-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one. 1H NMR δ 7.45-7.26 (m, 7H), 6.78-6.73 (d, 2H), 4.81 (s, 1H), 4.59 (s, 1H), 3.33-3.27 (m, 1H), 3.05-2.95 (m, 1H), 2.60-2.44 (m, 3H), 2.28-2.18 (m, 1H), 1.65 (s, 3H), 1.59 (s, 3H), 1.41 (s, 3H).

Workup

  1. customThe reaction was quenched with water (15 mL)
  2. extractionextracted with CH2Cl2 (15 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrate under vacuum
  6. customThe residue was purified by preparative TLC (petroleum ether: EtOAc =3:1)

Sources & evidence

ORD record
ord-99a9619c980242beaf1202d5f4573317
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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