Toluene → HCID 58843203, compound

HRID 1271003Notes

Reaction equation

HRID 1271003 reaction equation
C(O[C:6](=[O:28])[NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)/[CH:9]=[CH:10]\[C:11](=[O:20])[NH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)(C)(C)C.COC(=O)/C=C\[C@@H](NC(OC(C)(C)C)=O)C[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.NCC[N:54]1[CH2:58][CH2:57][CH2:56][CH2:55]1.C[Al](C)C.[C:63]1(C)C=CC=C[CH:64]=1>>[N:15]1([CH2:14][CH2:13][NH:12][C:11](=[O:20])/[CH:10]=[CH:9]\[C@@H:8]([NH:7][C:6]([NH:54][C:58]2[CH:57]=[CH:56][C:55]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:64][CH:63]=2)=[O:28])[CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 5

HCID 1140TolueneHCID 13441-PyrrolidineethanamineHCID 16682925TrimethylaluminumHCID 69432856HCID 69432856, compoundHCID 69433020HCID 69433020, compound

Product 1

HCID 58843203HCID 58843203, compoundYield 16%

Conditions

Temperature
25 °C

Procedure

[(Z)-(S)-1-Benzyl-3-(2-pyrrolidin-1-yl-ethylcarbamoyl)-allyl]-carbamic acid tert-butyl ester. To a solution of (Z)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester (0.10 g, 0.33 mmol) in toluene (3.6 mL) was added aminoethylpyrrolidine (0.041 g, 0.36 mmol) and trimethylaluminum (2 M in hexanes, 0.026 g, 0.36 mmol), and the solution was stirred (25° C., 4 h). The solvent was removed in vacuo, and the residue was partitioned with 1 N NaOH and CH2Cl2 (50 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography using 0–20% (1% NH4OH/MeOH in CH2Cl2) to provide the desired product as a clear oil (0.02 g, 16%): MS (electrospray): mass calculated for C22H33N3O3, 387.25; m/z found, 388.2 [M+H]+; 410.2 [M+Na]+. 1H NMR (CDCl3, 400 MHz): 7.20–7.25 (m, 2H), 7.13–7.18 (m, 3H), 5.72–5.81 (m, 2H), 5.08 (br s, 1H), 4.94 (br s, 1H), 3.28–3.45 (m, 2H), 2.91 (dd, J=13.4, 5.6 Hz, 1H), 2.77–2.86 (m, 1H), 2.51–2.61 (m, 2H), 2.42–2.47 (m, 4H), 1.65–1.71 (m, 4H), 1.32 (s, 9H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned with 1 N NaOH and CH2Cl2 (50 mL each)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-b3cad0a3574f44b0a5b1eadc86ee0cf4
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

Loading…