1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide → 1-[2-(4-Methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide
Reaction equation
C(OC([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:29])[CH:14]([NH:16][C:17](=[O:28])[C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25][CH3:26])=[C:20]([CH3:27])[CH:19]=1)[CH3:15])=O)(C)(C)C.[O:30]=[C:31]1[O:35][CH:34]([O:36][CH2:37][CH2:38]C2C=CC=CC=2)[CH:33]([NH:45][C:46](C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=[O:47])[CH2:32]1>>[CH2:37]([O:36][CH:34]1[CH:33]([NH:45][C:46]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:29])[CH:14]([NH:16][C:17](=[O:28])[C:18]2[CH:19]=[C:20]([CH3:27])[C:21]([O:25][CH3:26])=[C:22]([CH3:24])[CH:23]=2)[CH3:15])=[O:47])[CH2:32][C:31](=[O:30])[O:35]1)[CH3:38]Participants
3
Reactant 2
Product 1
Procedure
Prepared from 1-[2-(4-methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester and anti-(2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 168 mg (77% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.10-1.35 (m, 3H), 1.35-1.60 (m, 3H), 1.90-2.45 (m, 10H), 2.60-3.00 (m, H), 3.55-3.95 (m, 8H), 4.15-4.60 (m, 2H), 4.83-5.00 (m, H), 5.29 (s, H), 6.95-7.06 (m, H), 7.50 (s, 2H), 7.92 (d, H); retention time on analytical HPLC: 10.14 min; LC-MS: m/z=476 (M+H+).
Sources & evidence
- ORD record
- ord-70d2445b534c45c7a49e67c01a6ef085
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691848B2
Reaction notes
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