Diisopropylethylamine → HCID 69331416, compound

HRID 1058852Notes

Reaction equation

HRID 1058852 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.CO.C(Cl)Cl>C(OCCO)C>[C:26]1([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)[C:28]2[C:31](=[CH:29][N:25]=[CH:26][CH:28]=2)[CH:31]=[CH:29][N:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10638537Ethyl 4-amino-N-(tert-butoxycarbonyl)-L-phenylalaninateHCID 21226129Dichloromethane methanol

Product 1

HCID 69331416HCID 69331416, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Ethyl (S)-3-(4-aminophenyl)-2-[N-(t-butyloxycarbonyl)amino]propanoate (600 mg, 1.95 mmol), Intermediate 5 (350 mg, 2.13 mmol) and DIPEA (276 mg, 372 μl, 2.13 mmol) in 2-ethoxyethanol (0.5 ml) were stirred at 130° under N2 for several hours. The reaction was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml). The phases were separated and the aqueous layer re-extracted with EtOAc (3×30 ml). The combined organic extracts were washed with brine (10 ml), dried (MgSO4) and evaporated in vacuo to afford a dark oil. Chromatography (SiO2; 3% MeOH/DCM) gave the title compound as a dull orange foam (360 mg, 42%). δH (CDCl3) 9.19 (1H, s), 8.67 (1H, d, J 5.9 Hz), 8.24 (1H, d, J 5.8 Hz), 7.66 (1H, d, J 5.9 Hz), 7.65 (2H, d, J 8.5 Hz), 7.21 (1H, d, J 5.8 Hz), 7.16 (2H, d, J 8.5 Hz), 7.15 (1H, obscured s), 5.05-4.97 (1H, m), 4.60-4.51 (1H, m), 4.19 (2H, q, J 7.1 Hz), 3.17-3.04 (2H, m), 1.44 (9H, s), 1.27 (3H, t, J 7.1 Hz); m/z (ES+, 70V) 459 (MNa+), 437 (MH+).

Workup

  1. customThe reaction was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml)
  2. customThe phases were separated
  3. extractionthe aqueous layer re-extracted with EtOAc (3×30 ml)
  4. washThe combined organic extracts were washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto afford a dark oil

Sources & evidence

ORD record
ord-8a0fdc966dca4bdda4e7db4f2ed8c4f3
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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