D-Arabinose → HCID 67312005, compound

HRID 1809530Notes

Reaction equation

HRID 1809530 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[C:6]([C:11]3[N:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH:23]=4)[C:21]#[N:22])[O:13][N:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH:28][C@@H:29]([C@H:32]([OH:37])[C@H:33]([OH:36])[CH2:34]O)[CH:30]=[O:31].[BH4-].[Na+]>CO.C(O)(=O)C>[CH:25]([O:24][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[O:13][N:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH2:4][CH2:3][C@@H:2]4[NH:1][CH2:34][C@H:33]([OH:36])[C@@H:32]([OH:37])[C@H:29]([OH:28])[CH2:30][OH:31])[N:15]=2)=[CH:23][C:20]=1[C:21]#[N:22])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 66308D-ArabinoseHCID 4311764Sodium borohydrideHCID 52938426Benzonitrile, 5-[3-[(1S)-1-amino-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)-

Product 1

HCID 67312005HCID 67312005, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Prepared using General Procedure 13. To a solution of (S)-5-(3-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 50 (50.mg, 0.14 mmol) in MeOH (10 mL) was added (2S,3R,4R)-2,3,4,5-tetrahydroxypentanal (20.71 mg, 0.14 mmol) and acetic acid (2 drops) with stirring at 50° C. for 18 h. The reaction was cooled to room temperature and sodium borohydride (52.2 mg, 1.38 mmol) was added slowly with stirring for 2 hours at room temperature. The reaction mixture was quenched with saturated NaHCO3 aqueous (10 mL) and extracted with EA (3×10 mL). The organic layers were washed with brine and dried over Mg2SO4. The product was purified by preparative HPLC to give 8.68 mg (25%) of 2-isopropoxy-5-(3-((S)-1-(((2S,3R,4R)-2,3,4,5-tetrahydroxypentyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)benzonitrile 119 as a solid. LCMS-ESI (m/z) calculated for C26H30N4O6: 494.5; found 495.2 [M+H]+, tR=2.42 min.

Workup

  1. customPrepared
  2. temperatureThe reaction was cooled to room temperature
  3. stirringwith stirring for 2 hours at room temperature
  4. customThe reaction mixture was quenched with saturated NaHCO3 aqueous (10 mL)
  5. extractionextracted with EA (3×10 mL)
  6. washThe organic layers were washed with brine
  7. dry with materialdried over Mg2SO4
  8. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c88e2ebec3974bb1a864270952e67305
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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