1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-butoxy-5-oxo-tetrahydro-furan-3-yl)-amide
Reaction equation
C(OC(C1CCCN1C(=O)C(NC(=O)C1C=CC(N)=C(Cl)C=1)C)=O)(C)(C)C.[O:28]=[C:29]1[O:33][CH:32]([O:34][CH2:35][CH2:36][C:37]2C=CC=C[CH:38]=2)[CH:31]([NH:43][C:44]([CH:46]2[CH2:50][CH2:49][CH2:48][N:47]2[C:51](=[O:65])[CH:52]([NH:54][C:55](=[O:64])[C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([Cl:63])[CH:57]=2)[CH3:53])=[O:45])[CH2:30]1>>[CH2:35]([O:34][CH:32]1[CH:31]([NH:43][C:44]([CH:46]2[CH2:50][CH2:49][CH2:48][N:47]2[C:51](=[O:65])[CH:52]([NH:54][C:55](=[O:64])[C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([Cl:63])[CH:57]=2)[CH3:53])=[O:45])[CH2:30][C:29](=[O:28])[O:33]1)[CH2:36][CH2:37][CH3:38]Participants
3
Reactant 2
Product 1
Procedure
Prepared from 97a and syn-(2-butoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 118 mg (48% yield) of the title compound as a syn diastereomer. 1H-NMR (500 MHz, CDCl3): δ 0.80-1.02 (m, 2H), 1.35-1.51 (m, 5H), 1.51-1.70 (m, 2H), 1.90-2.27 (m, 3H), 2.30-2.46 (m, H), 2.80-2.90 (m, H), 3.55-3.94 (m, 4H), 4.30-4.75 (m, 4H), 4.90-5.00 (m, H), 5.44-5.46 (m, H), 6.73-6.80 (m, H), 6.80-6.93 (m, H), 7.16-7.25 (m, H), 7.49-7.60 (m, H), 7.70-7.84 (m, H); retention time on analytical HPLC: 9.71 min; LC-MS: m/z=495 (M+H+).
Sources & evidence
- ORD record
- ord-2dabbc0ea4664aeabf3baf5360cc2c5b
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07358273B2
Reaction notes
Loading…