Triethylamine → Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate

HRID 1192901Notes

Reaction equation

HRID 1192901 reaction equation
[NH2:1][C:2]1([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[CH2:23]([C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[O:39])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:2]1([NH:1][C:38]([NH:37][C:34]2[CH:35]=[CH:36][C:31]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:32][CH:33]=2)=[O:39])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37026561-Isocyanato-4-octylbenzeneHCID 66864898Benzyl 3-amino-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66865221Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 3-amino-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate (260 mg, 0.85 mmol) and p-octylphenylisocyanate (215 mg, 0.93 mmol) in CH2Cl2 (3 mL) was added triethylamine (0.35 mL, 2.55 mmol) to give the title compound as a brown solid (140 mg, 31%). MS ESI 538.2 [M+H]+, calcd for [C31H43N3O5+H] 538.32.

Sources & evidence

ORD record
ord-4b6dee1723b841038c04c028c1edb380
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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