Formaldehyde → HCID 69037992, compound

HRID 351383Notes

Reaction equation

HRID 351383 reaction equation
[CH:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]3([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[O:21][CH2:20][CH2:19][O:18]3)[C:12]2=[O:32])[C@H:7]([CH2:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH2:6]1)([CH3:3])[CH3:2].C=O.[C:45]([BH3-])#N.[Na+]>CO.CCOC(C)=O>[CH:1]([N:4]([CH3:45])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]3([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=4)[O:21][CH2:20][CH2:19][O:18]3)[C:12]2=[O:32])[C@H:7]([CH2:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:35])=[O:36])[CH2:6]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69039943HCID 69039943, compound

Product 1

HCID 69037992HCID 69037992, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 39i-b (103 mg, 168 μmol) and 37% formaldehyde (50 μL, 1.8 mmol) were dissolved in MeOH (2 mL) and stirred for 3 h at room temperature. Sodium cyanoborohydride (16 mg, 252 μmol) was added and the mixture was stirred for 2 h. The reaction was diluted with EtOAc (400 mL), washed with saturated NaHCO3 (3×150 mL) and brine (100 mL), dried over Na2SO4, filtered, and evaporated. The residue was purified by CombiFlash chromatography (silica, 0–10% CH2Cl2/MeOH) and then lyophilized from CH3CN/H2O to give title compound (77 mg, 74%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.90–7.82 (m, 2H), 7.71 (s, 1H), 7.68–7.42 (m, 6H), 4.15–3.92 (m, 3H), 3.80–3.00 (m, 7H), 2.71–2.10 (m, 9H), 1.93–1.40 (m, 9H), 1.17–0.95 (m, 6H); 19F NMR (282 MHz, CDCl3) δ −62.9; ESI MS m/z 623 [C32H41F3N2O5S+H]+.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. washwashed with saturated NaHCO3 (3×150 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by CombiFlash chromatography (silica, 0–10% CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-22075826890c4eb19deb6b1086fdc6ae
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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