3-Chloro-4-dimethylamino-benzoic acid → 1-[2-(3-Chloro-4-dimethylamino-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 2363406Notes

Reaction equation

HRID 2363406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]([CH3:13])[CH3:12])[C:5]([OH:7])=O.[O:14]=[C:15]1[O:19][CH:18]([O:20][CH2:21][CH2:22][C:23]2C=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:37](=[O:51])[CH:38]([NH:40]C(=O)C2C=CC(N)=C(Cl)C=2)[CH3:39])=[O:31])[CH2:16]1>>[CH2:21]([O:20][CH:18]1[CH:17]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:37](=[O:51])[CH:38]([NH:40][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([N:11]([CH3:13])[CH3:12])=[C:2]([Cl:1])[CH:3]=2)[CH3:39])=[O:31])[CH2:16][C:15](=[O:14])[O:19]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 186236883-Chloro-4-dimethylamino-benzoic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide

Product 1

HCID 229777701-[2-(3-Chloro-4-dimethylamino-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 44%

Procedure

Prepared from {2-[2-(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbmoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester and 3-chloro-4-dimethylamino-benzoic acid according to the procedure used to prepare 98a to afford 82 mg of title compound (44% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.18-1.53 (m, 3H), 1.70-2.40 (m, 4H), 2.55-3.10 (m, 2H), 2.84 (s, 6H), 3.45-3.94 (m, 2H), 4.25-4.95 (m, 5H), 5.46 (s, 0.3H), 5.51 (s, 0.2H), 5.63 (d, 0.4H), 5.73 (d, 0.1H), 7.05 (d, 1H), 7.15-7.95 (m, 7H). Analytical HPLC: 11.85, 12.19 min. LC-MS (ES+): m/e=557.3 (M+H+).

Sources & evidence

ORD record
ord-cf458c90c2564edfac6628977391c6e7
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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