HCID 18623633, compound → HCID 22977485, compound

HRID 900590Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:25]([Cl:26])=[CH:24][C:8]([C:9]([NH:11][CH:12]([CH3:23])[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2C(O)=O)=[O:14])=[O:10])=[C:7]([O:27][CH3:28])[CH:6]=1)(=[O:3])[CH3:2].[O:29]=[C:30]1[O:34][CH:33]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40]C=2)[CH:32]([NH:44][C:45](C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=[O:46])[CH2:31]1>>[CH2:36]([O:35][CH:33]1[CH:32]([NH:44][C:45]([CH:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:13](=[O:14])[CH:12]([NH:11][C:9](=[O:10])[C:8]2[CH:24]=[C:25]([Cl:26])[C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=2[O:27][CH3:28])[CH3:23])=[O:46])[CH2:31][C:30](=[O:29])[O:34]1)[C:37]1[CH:38]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Reactant 2

HCID 18623633HCID 18623633, compound

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

Product 1

HCID 22977485HCID 22977485, compoundYield 82%

Procedure

Prepared from syn-{2-[2-(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester and 97c following the procedure used for 98a to afford the title compound (222 mg, 82% yield). 1H-NMR (500 MHz, CD3OD) δ 1.23 (d, 0.6H), 1.42 (d, 2.4H), 1.72-2.27 (m, 4H), 2.23 (s, 3H), 2.63 (dd, 1H), 2.77-2.88 (m, 1H), 3.43-3.52 (m, 0.5H), 3.56-3.71 (m, 1.5H), 3.74-3.85 (m, 1H), 3.98 (s, 3H), 4.38-4.50 (m, 1.5H), 4.51-4.92 (m, 4.5H), 5.63-5.76 (m, 1H), 7.23-7.40 (m, 5H), 7.97 (s, 1H), 8.45 (d, 1H), 8.69-8.80 (m, 1H) Analytical HPLC 11.63 min LC-MS (ES+) m/e=601.2 (MH+).

Sources & evidence

ORD record: ord-ecf80363beea41a8861c3eda13333855
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358273B2

Reaction notes

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