(2-Isopropoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-isopropoxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900595Notes

Reaction equation

HRID 900595 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH:9]([CH3:20])[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[C:17]([OH:19])=O)=[O:11])=[O:7])=[CH:4][C:3]=1[Cl:23].C(OC(=O)[NH:29][CH:30]1[CH2:34][C:33](=[O:35])[O:32][CH:31]1[O:36][CH:37]([CH3:39])[CH3:38])C=C.O=C1OC(OCCC2C=CC=CC=2)C(NC(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)C1>>[CH:37]([O:36][CH:31]1[CH:30]([NH:29][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][N:12]2[C:10](=[O:11])[CH:9]([NH:8][C:6](=[O:7])[C:5]2[CH:21]=[CH:22][C:2]([NH2:1])=[C:3]([Cl:23])[CH:4]=2)[CH3:20])=[O:19])[CH2:34][C:33](=[O:35])[O:32]1)([CH3:39])[CH3:38]

Participants

4

Reactant 3

HCID 18465855(2-Isopropoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 186236851-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide

Product 1

HCID 229775101-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-isopropoxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 66%

Procedure

Prepared from 97a and (2-isopropoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 200 mg of title compound (66% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.05-1.35 (m, 6H), 1.35-1.50 (m, 3H), 1.70-2.45 (m, 4H), 2.45-3.05 (m, 2H), 3.55-4.10 (m, 3H), 4.15-4.88 (m, 4H), 5.48 (s, 0.4H), 5.58 (s, 0.1H), 5.64 (d, 0.4H), 5.70 (d, 0.1H), 6.78 (d, 1H), 7.58 (d, 1H), 7.80 (s, 1H). Analytical HPLC: 12.19, 12.40 min. LC-MS (ES+): m/e=581.2 (M+H+).

Sources & evidence

ORD record
ord-e308750ccfbf4d9c9c39524e0be94437
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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