Sodium Bicarbonate → HCID 86708054, compound

HRID 1524351Notes

Reaction equation

HRID 1524351 reaction equation
[CH2:1]([O:8][C:9](=[O:42])[N:10]([C@@H:16]([CH2:36][CH2:37][CH:38]([F:41])[CH2:39][NH2:40])[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[CH3:48][O:49][C:50]([NH:52][C@H:53]([C:67](ON1C(=O)CCC1=O)=[O:68])[CH:54]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:51]>C1COCC1.O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9](=[O:42])[N:10]([C@@H:16]([CH2:36][CH2:37][CH:38]([F:41])[CH2:39][NH:40][C:67](=[O:68])[C@H:53]([CH:54]([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[NH:52][C:50]([O:49][CH3:48])=[O:51])[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:33])[CH3:34])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 579092872,5-Dioxopyrrolidin-1-yl N-(methoxycarbonyl)-beta-phenyl-L-phenylalaninateHCID 86708052HCID 86708052, compound

Product 1

HCID 86708054HCID 86708054, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of the material from Step 10 (86 mg, 0.145 mmol) in THF (1 mL) and water (333 μL) at 0° C. was added NaHCO3 (49 mg, 0.58 mmol) and followed by portionwise addition of 2,5-dioxopyrrolidin-1-yl N-(methoxycarbonyl)-β-phenyl-L-phenylalaninate (63 mg, 0.16 mmol). The reaction mixture was stirred at room temperature overnight, poured into brine, and extracted with EtOAc (2×). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 110 mg of the title compound. 1H NMR (DMSO-d6): δ 8.24-8.12 (m, 1H), 7.67-7.53 (m, 4H), 7.51-7.37 (m, 6H), 7.37-7.20 (m, 11H), 7.19-7.07 (m, 2H), 7.03-6.91 (m, 1H), 5.15-4.90 (m, 3H), 4.29-4.19 (m, 1H), 3.96-3.76 (m, 1H), 3.74-3.47 (m, 2H), 3.06 (s, 3H), 3.16-2.97 (m, 4H), 2.96-2.76 (m, 1H), 1.55-1.28 (m, 5H), 1.27-1.01 (m, 2H), 0.97 (s, 9H), 0.85 (d, J=4.2 Hz, 3H), 0.77 (d, J=4.20 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b34399271c594952a42cdbfb11beedb3
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

Loading…