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 syn-(2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 174 mg (81% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.04 (t, 0.45H), 1.27 (t, 2.55H), 1.34-1.45 (m, 3H), 1.95-2.45 (m, 10H), 2.78-2.84 (m, H), 3.60-3.90 (m, 8H), 4.50-4.70 (m, 2H), 4.90-4.94 (m, H), 5.45 (d, 0.85H), 5.61 (d, 0.15H), 6.99 (d, H), 7.15 (d, H), 7.45 (s, 2H); retention time on analytical HPLC: 10.09 min; LC-MS: m/z=476 (M+H+).
Sources & evidence
- ORD record
- ord-85f1a72913ca4129919310f2e326fb06
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691848B2
Reaction notes
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