1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid → HCID 22977501, compound

HRID 1861267Notes

Reaction equation

HRID 1861267 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].[O:24]=[C:25]1[O:29][CH:28]([O:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=CC=2)[CH:27]([NH:39]C(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)[CH2:26]1>>[CH:31]1([O:30][CH:28]2[CH:27]([NH:39][C:17]([CH:13]3[CH2:14][CH2:15][CH2:16][N:12]3[C:10](=[O:11])[CH:9]([NH:8][C:6](=[O:7])[C:5]3[CH:21]=[CH:22][C:2]([NH2:1])=[C:3]([Cl:23])[CH:4]=3)[CH3:20])=[O:19])[CH2:26][C:25](=[O:24])[O:29]2)[CH2:32][CH2:33][CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 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 22977501HCID 22977501, compoundYield 47%

Procedure

Prepared from syn-(2-cyclohexyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 97a following the method used for 98a to give the title compound (153 mg, 47% yield). 1H-NMR (500 MHz, CD3OD) δ 1.06-2.38 (m, 14H), 1.42 (d, 3H), 2.50-2.66 (m, 1H), 2.69-2.82 (dd, 1H), 3.06-3.75 (m, 2H), 3.80-3.94 (m, 1H), 4.40-4.52 (m, 1H), 4.57-4.65 (m, 1H), 4.70-4.80 (m, 1H), 5.72 (d, 1H), 6.71 (m, 1H), 7.50-7.63 (m, 1H), 7.78 (d, 0.6H), 8.42 (d, 0.4H). Analytical HPLC 10.30 min. LC-MS (ES+) m/e=521.2 (MH+).

Sources & evidence

ORD record
ord-5f9b2090fbfb4967bdf430083aa5d830
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

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