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

HRID 2363415Notes

Reaction equation

HRID 2363415 reaction equation
C(O[C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH:14]([NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([Cl:25])[CH:19]=1)[CH3:15])=[O:7])(C)(C)C.[O:28]=[C:29]1[O:33][CH:32]([O:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39]C=2)[CH:31]([NH:43]C(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)[CH2:30]1>>[CH:36]1([CH2:35][O:34][CH:32]2[CH:31]([NH:43][C:6]([CH:8]3[CH2:12][CH2:11][CH2:10][N:9]3[C:13](=[O:27])[CH:14]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([Cl:25])[CH:19]=3)[CH3:15])=[O:7])[CH2:30][C:29](=[O:28])[O:33]2)[CH2:37][CH2:42][CH2:41][CH2:40][CH2:39]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 536934251-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 22977502(2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclohexylmethoxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 56%

Procedure

Prepared from 97a and syn-(2-cyclohexylmethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 113 mg (56% yield) of the title compound. 1H-NMR-(500 MHz, CDCl3): δ 0.70-1.35 (m, 5H), 1.35-1.90 (m, 8H), 1.90-2.20 (m, 3H), 2.30-2.60 (m, H), 2.80-3.00 (m, H), 3.15-3.80 (m, 4H), 4.28-4.75 (m, 4H), 4.89-4.93 (m, H), 5.42 (d, H), 6.74 (d, H), 6.87 (d, H), 7.30 (d, H), 7.51-7.53 (m, H), 7.74 (d, H); retention time on analytical HPLC: 12.02 min; LC-MS: m/z=535 (M+H+).

Sources & evidence

ORD record
ord-6aac77e7c66b41d88bcc9a52b3f269d2
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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