Ammonium Chloride → HCID 86345811, compound

HRID 1772743Notes

Reaction equation

HRID 1772743 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[N:25]4[CH:26]=[C:27]([C:29](OCC)=[O:30])[N:28]=[C:24]4[C:23]([N:34]4[CH2:39][CH2:38][S:37](=[O:41])(=[O:40])[CH2:36][CH2:35]4)=[N:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[O:41]=[S:37]1(=[O:40])[CH2:38][CH2:39][N:34]([C:23]2[C:24]3[N:25]([CH:26]=[C:27]([CH2:29][OH:30])[N:28]=3)[C:20]([C:17]3[CH:16]=[CH:15][C:14]([N:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]4)=[N:19][CH:18]=3)=[CH:21][N:22]=2)[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 86345947HCID 86345947, compound

Product 1

HCID 86345811HCID 86345811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 89a (107 mg, 0.183 mmol) in 18 mL of THF at 0° C. was added LiAlH4 (0.183 mL, 0.183 mmol, 1.0M in THF). The reaction was stirred at 0° C. for 3 h. The mixture was treated with 20 mL of saturated NH4Cl solution and then extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel (0-100% EtOAc/heptane) to give compound 89b as an off white solid. 1H-NMR (2:1 CDCl3/CD3OD; 400 MHz) δ: 8.34 (s, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 7.34 (s, 1H), 6.88 (d, J=8.8 Hz, 1H), 4.78 (br. s., 6H), 3.68 (d, J=3.2 Hz, 4H), 3.60 (br. s., 4H), 3.23 (br. s., 4H), 1.51 (s, 9H). Mass spectrum (LCMS, ESI pos.): Calcd. for C25H33N7O5S, 544.2 (M+H). found 544.3.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography on silica gel (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-1b98ad8c768a4e5f995b6f867e422da4
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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