Triethylamine → HCID 59437174, compound

HRID 75151Notes

Reaction equation

HRID 75151 reaction equation
[CH:1]1([C@H:7]([OH:21])[CH2:8][NH:9][CH2:10][C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:11]12([CH2:10][N:9]3[CH2:8][C@H:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[O:21][C:30]3=[O:32])[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 59437170HCID 59437170, compound

Product 1

HCID 59437174HCID 59437174, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1-cyclohexyl-2-((1-adamantylmethyl)amino)ethanol (22 mg, 0.077 mmol) and Et3N (15.6 mg, 0.154 mmol) in dry CH2Cl2(2 mL) at 0° C. was added triphosgene (9.2 mg, 0.031 mmol) in dry CH2Cl2(2 mL). The mixture was stirred for 30 min and then concentrated in vacuum to give the crude product, which was purified by preparative TLC to afford (S)-3-((1-adamantyl)methyl)-5-cyclohexyloxazolidin-2-one (5 mg, 21%). 1H NMR (MeOD, 400 MHZ): δ=1.18-1.97 (m, 25H), 2.75-2.95 (m, 2H), 3.42 (t, 1H), 3.72 (t, 1H), 4.83 (m, 1H); MS: m/z=318.

Workup

  1. concentrationconcentrated in vacuum
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-26e2830683244d6b9e9d51959b71873f
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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