Hydrochloric Acid → HCID 71624775, compound

HRID 415353Notes

Reaction equation

HRID 415353 reaction equation
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]2[C:13]([NH:14][C@H:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:16][OH:17])=[N:12][C:11]([SH:22])=[N:10][C:9]=2[N:23]=1.[ClH:24]>O.CC#N>[Cl:24][C:6]1[S:7][C:8]2[C:13]([NH:14][C@H:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:16][OH:17])=[N:12][C:11]([S:22][S:22][C:11]3[N:12]=[C:13]([NH:14][C@@H:15]([CH2:16][OH:17])[CH2:18][CH:19]([CH3:20])[CH3:21])[C:8]4[S:7][C:6]([Cl:24])=[N:23][C:9]=4[N:10]=3)=[N:10][C:9]=2[N:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178445911HCID 178445911, compound

Product 1

HCID 71624775HCID 71624775, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

Sodium nitrite (5.19 g, 75 mmol) in water (25 mL) was added dropwise at 0° C. to (2R)-2-[[2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol (7.50 g, 25 mmol) in conc. HCl (150 mL) and CH3CN (150 mL). The reaction mixture was stirred for 18 h at 0-5° C., and then poured onto ice (500 mL), and extracted with EtOAc. Any remaining solid was filtered off. The combined organic phases were washed sequentially with saturated NaCl solution and saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated and the solid previously filtered off was added to this. The total solid was slurried in EtOAc, which after filtration provided the title compound (6.3 g, 80% yield) as a solid.

Workup

  1. additionpoured onto ice (500 mL)
  2. extractionextracted with EtOAc
  3. filtrationAny remaining solid was filtered off
  4. washThe combined organic phases were washed sequentially with saturated NaCl solution and saturated aqueous NaHCO3 solution
  5. customThe organic phase was dried
  6. customevaporated
  7. filtrationthe solid previously filtered off
  8. additionwas added to this
  9. filtrationwhich after filtration

Sources & evidence

ORD record
ord-254629d8ca624effa34d306a1b7fd2c1
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Reaction notes

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