Triethylamine → HCID 69598118, compound

HRID 724590Notes

Reaction equation

HRID 724590 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:23](=[O:25])(=[O:24])[N:22](C(C)(C)C)[C:21](=[O:30])[CH:20]=2)=[CH:15][CH:14]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:5].[N:31]([C@@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([O:37]C)=[O:36])=[C:32]=[O:33].C(N(CC)CC)C>CN(C)C=O>[CH2:7]([NH:6][C:4]([C@@H:3]([NH:2][C:32](=[O:33])[NH:31][C@@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([OH:37])=[O:36])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:23](=[O:25])(=[O:24])[NH:22][C:21](=[O:30])[CH:20]=2)=[CH:15][CH:14]=1)=[O:5])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514293Methyl N-(oxomethylidene)phenylalaninateHCID 69597981HCID 69597981, compound

Product 1

HCID 69598118HCID 69598118, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 9-E (150 mg, 0.33 mmol), methyl (S)-(−)-2-isocyanato-3-phenylpropionate (120 μL, 0.66 mmol), and triethylamine (140 μL, 0.99 mmol) in dimethylformamide (2 mL) was stirred at 25° C. for 16 h. The reaction mixture was treated with Triamine-3 functionalized silica gel (1.2 mmol) and stirred for 1 h. The reaction mixture was filtered through a short plug of silica gel and washed with ethyl acetate (10 mL). The filtrate was concentrated and used without further purification. The crude product was dissolved in trifluoroacetic acid (10 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated and purified using preparative LCMS to yield the product (29 mg, 15%) as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.83 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 2H), 7.31–7.28 (m, 2H), 7.25–7.22 (m, 1H), 7.18 (dd, J=8.3, 1.5 Hz, 2H), 7.02 (s, 1H), 4.53 (dd, J=7.8, 5.9 Hz, 1H), 4.44 (dd, J=7.3, 6.8 Hz, 1H), 3.69 (s, 3H), 3.19–3.04 (m, 4H), 3.00–2.94 (m, 2H), 1.42–1.35 (m, 2H), 1.34–1.28 (m, 2H), 1.24–1.19 (m, 2H), 0.90 (t, J=7.3 Hz, 3H); LCMS found for C28H35N4O7S (M+H)+: m/z=571.

Workup

  1. filtrationThe reaction mixture was filtered through a short plug of silica gel
  2. washwashed with ethyl acetate (10 mL)
  3. concentrationThe filtrate was concentrated
  4. customused without further purification
  5. dissolutionThe crude product was dissolved in trifluoroacetic acid (10 mL)
  6. concentrationThe reaction mixture was concentrated
  7. custompurified

Sources & evidence

ORD record
ord-29ca3fdd07b24da1a3e48b7ee73f56be
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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