Triethylamine → HCID 58720989, compound

HRID 1246384Notes

Reaction equation

HRID 1246384 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C@@H:10]([C@H:25]([CH3:28])[CH2:26][CH3:27])[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(Cl)Cl>[CH3:28][C@@H: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)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 13494759HCID 13494759, compound

Product 1

HCID 58720989HCID 58720989, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trichloromethyl chloroformate (5.4 g, 27.3 mmol) was added to a mixture of (S)-2-amino-1,1-diphenyl-3-methylpentan-1-ol 13 (4.97 g of 60%, 11.1 mmol) and triethylamine (5.3 g, 52.0 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 3 h at 0° C., then allowed to warm to room temperature for 18 h. The mixture was then washed with HCl (3×100 ml) and water (2×100 ml) and dried over MgSO4. Concentration gave a crude product, which was washed with diethyl ether to afford the title compound 14 (2.7 g, 83%) as a white amorphous solid. m.p. 221–223° C. [α]D25=−243.9° (c, 4.33 in CHCl3). δH 0.41 (3H, t, J=7.2 Hz, CH3), 0.80 (3H, d, J=6.9 Hz, CH3), 0.80–0.96 (1H, m, CH2), 1.18–1.32 (1H, m, CH—Me), 1.34–1.50 (1H, m, CH2), 4.27 (1H, d, J=3.6 Hz, CH—NH), 6.98 (1H, s, NH), 7.10–7.50 (10H, m, Ar—H). δC 11.3 (CH3—CH2), 17.2 (CH3—CH), 22.7 (CH2), 36.3 (CH—Me), 66.1 (CH—NH), 89.5 (C), 125.9, 126.5, 127.7, 128.0, 128.3, 128.6, 139.3, 144.0 (Ar), 159.1 (C═O). νmax (cm−1): 3281, 3162 (N—H), 3058 (Ar C—H), 2980, 2960, 2933, 2877 (methyl and methylene C—H), 1760, 1725 (C═O), 1493, 1448 (Ar C═C), 1243 (C—O). m/e 313 (MNH4+, 6%), 296 (MH+, 8%), 237 (100%).

Workup

  1. temperatureto warm to room temperature for 18 h
  2. washThe mixture was then washed with HCl (3×100 ml) and water (2×100 ml)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration
  5. customgave a crude product, which
  6. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-78f223c85b0648918adf9c77ed80f533
Source dataset
uspto-grants-2006_10
Patent number
US07126028B1

Reaction notes

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