Acetic Acid → HCID 90801850, compound

HRID 2377264Notes

Reaction equation

HRID 2377264 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:30]3[S:34][C:33]([CH:35]=O)=[CH:32][CH:31]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.[CH3:45][NH2:46].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[CH3:44][O:43][C:40]1[CH:41]=[CH:42][C:37]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:30]3[S:34][C:33]([CH2:35][NH:46][CH3:45])=[CH:32][CH:31]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:17][CH:16]=4)=[CH:38][CH:39]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 87732437HCID 87732437, compound

Product 1

HCID 90801850HCID 90801850, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 331 (1.2 g, 2.0 mmol) in methanol (10 mL) and tetrahydrofuran (5 mL) added a 2M solution of methylamine in tetrahydrofuran (5 mL) and acetic acid (0.6 mL, 10 mmol). Then sodium triacetoxyborohydride (1.25 g, 6 mmol) was added and the mixture was stirred at room temperature for about 5 hours. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium carbonate and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (10:1)+1% ammonium hydroxide as eluent to provide the desired product. MS (ESI): m/z 620 (M+H)+.

Workup

  1. washwashed with saturated aqueous sodium carbonate
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-69085606060b42eeaf35e5be2a0949c4
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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