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 900604Notes

Reaction equation

HRID 900604 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-88771ca0e11b46afba78c895a2326f7d
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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