1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide → HCID 22977774, compound

HRID 900609Notes

Reaction equation

HRID 900609 reaction equation
C(OC([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:28])[CH:14]([NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1)[CH3:15])=O)(C)(C)C.[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:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:28])[CH:14]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([N:24]([CH3:25])[CH3:26])=[CH:20][CH:19]=2)[CH3:15])=[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

3

Reactant 2

HCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 54359099HCID 54359099, compound

Product 1

HCID 22977774HCID 22977774, compoundYield 45%

Procedure

Prepared from 1-[2-(4-dimethylamino-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester and syn-(2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 60 mg (45% yield). 1H-NMR (500 MHz, CDCl3): δ 1.04 (d, 0.75H), 1.35 (d, 2.25H), 1.80-2.50 (m, 5H), 2.75-3.20 (m, 8H), 3.45-3.75 (m, 2H), 4.05-4.20 (m, 0.5H), 4.30-4.80 (m, 3.5H), 4.80-4.95 (m, 1.5H), 5.52 (d, H), 5.75-6.00 (m, 0.5H), 6.60-6.90 (m, 3H), 7.10-7.50 (m, 4H), 7.50-7.80 (m, 2H); retention time on analytical HPLC: 10.46 min; LC-MS: m/z=523 (M+H+).

Workup

  1. customto afford 60 mg (45% yield)
  2. custom10.46 min

Sources & evidence

ORD record
ord-2e035f5c3c12414e96f0e04dd4ca2fe2
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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