Pivaloyl chloride → 1-{2-[3-Chloro-4-(2,2-dimethylpropionylamino)-benzoylamino]-propionyl}-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 1861283Notes

Reaction equation

HRID 1861283 reaction equation
[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:36])[CH:23]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[C:29]([Cl:34])[CH:28]=2)[CH3:24])=[O:16])[CH2:12][C:11](=[O:37])[O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](Cl)(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>>[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:36])[CH:23]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])=[C:29]([Cl:34])[CH:28]=2)[CH3:24])=[O:16])[CH2:12][C:11](=[O:37])[O:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 62493Pivaloyl chlorideHCID 229774991-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

Product 1

HCID 229777671-{2-[3-Chloro-4-(2,2-dimethylpropionylamino)-benzoylamino]-propionyl}-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 85%

Procedure

To a suspension of 98b (100 mg, 0.19 mmol) and poly(4-vinylpyridine) (200 mg) was added pivaloyl chloride (70 μL, 0.57 mmol). The resulting suspension was stirred overnight at room temperature the filtered and diluted with EtOAc (25 mL). The organic layer was washed with 10% NaHCO3 (2×25 mL), saturated NaCl (1×25 mL), dried (MgSO4), and evaporated to dryness to afford 98 mg of title compound (85% yield) after chromatography. 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.10-1.55 (m, 3H), 1.38 (s, 9H), 1.65-2.40 (m, 4H), 2.60-3.10 (m, 2H), 3.46-3.88 (m, 2H), 4.20-4.95 (m, 5H), 5.62 (d, 0.8H), 5.78 (d, 0.2H), 7.15-8.30 (m, 8H). Analytical HPLC: 11.82 min. LC-MS (ES+): m/e=613.2 (M+H+).

Workup

  1. filtrationfiltered
  2. additiondiluted with EtOAc (25 mL)
  3. washThe organic layer was washed with 10% NaHCO3 (2×25 mL), saturated NaCl (1×25 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e55e260722d5472aa856fef7bd57c441
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

Loading…