Sodium Bicarbonate → HCID 118348002, compound

HRID 2273608Notes

Reaction equation

HRID 2273608 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:30]([S:33]([N:36]1[CH2:41][CH2:40][N:39]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:66])[C:51]3[CH:56]=[CH:55][C:54](B4OC(C)(C)C(C)(C)O4)=[CH:53][CH:52]=3)=[CH:45][CH:44]=2)[CH2:38][CH2:37]1)(=[O:35])=[O:34])[CH2:31][CH3:32].C([O-])(O)=O.[Na+]>COCCOC.O>[CH2:25]([S:22]([N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]([C:5]3[CH:28]=[CH:29][C:2]([C:54]4[CH:55]=[CH:56][C:51]([C:50]([NH:49][C:46]5[CH:47]=[CH:48][C:43]([CH2:42][N:39]6[CH2:40][CH2:41][N:36]([S:33]([CH2:30][CH2:31][CH3:32])(=[O:34])=[O:35])[CH2:37][CH2:38]6)=[CH:44][CH:45]=5)=[O:66])=[CH:52][CH:53]=4)=[CH:3][CH:4]=3)=[O:7])=[CH:10][CH:11]=2)[CH2:17][CH2:18]1)(=[O:24])=[O:23])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 118348015HCID 118348015, compoundHCID 131733388HCID 131733388, compound

Product 1

HCID 118348002HCID 118348002, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture containing 5 (88.8 mg, 0.18 mmol), 6 (101.4 mg, 0.19 mmol), Pd(TPP)4 (9.1 mg, 0.008 mmol), and NaHCO3 (57.1 mg, 0.68 mmol) in DME/H2O (4.5:1 v/v, 7 mL) was heated at 80° C. for 19 h, allowed to cool to rt, and evaporated to dryness. The remaining crude product was washed with H2O (3×10 mL) and dried, then a portion (60.5 mg of the 178.1 mg isolated) was purified by PTLC to give the title product (21.9 mg). Rf 0.38 (100:10:1 v/v CHCl3/MeOH/NH4OH (28%)). HPLC: tR 1.68 min (method 1). LC-MS m/z calcd for C42H52N6O6S2 ([M]+), 800. found, 801 ([M+H]+). 1H NMR (DMSO-d6): δ 0.92 (t, J=7.5 Hz, 3H), 1.62 (m, 2H), 2.38 (m, 4H), 2.95 (m, 2H), 3.10 (m, 4H), 3.44 (br s, 2H), 7.23 (m, 2H), 7.70 (m, 2H), 7.87 (m, 2H), 8.03 (m, 2H), 10.25 (s, 1H).

Workup

  1. temperatureto cool to rt
  2. customevaporated to dryness
  3. washThe remaining crude product was washed with H2O (3×10 mL)
  4. customdried
  5. customa portion (60.5 mg of the 178.1 mg isolated)
  6. customwas purified by PTLC

Sources & evidence

ORD record
ord-18c26743968b40b68f5cc7e8d5c252b4
Source dataset
uspto-grants-2015_09
Patent number
US09125904B1

Reaction notes

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