Hydrochloric Acid → 3-[(3R)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]-2-hydroxypropanenitrile

HRID 1503985Notes

Reaction equation

HRID 1503985 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]2[C:13]=1[C:12]1[C@@H:11]([CH2:14][CH:15]([O:18][Si](C)(C)C)[C:16]#[N:17])[CH2:10][CH2:9][C:8]=1[S:7]2.Cl.C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]2[C:13]=1[C:12]1[C@@H:11]([CH2:14][CH:15]([OH:18])[C:16]#[N:17])[CH2:10][CH2:9][C:8]=1[S:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 896913113-[(3R)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]-2-[(trimethylsilyl)oxy]propanenitrile

Product 1

HCID 896940583-[(3R)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]-2-hydroxypropanenitrileYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(3R)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]-2-[(trimethylsilyl)oxy]propanenitrile (240 mg, 0.68 mmol, 1.00 equiv) in methanol (5 mL) was added 1 mL of concentrated hydrochloric acid at 0° C. After stirring for 1 h at room temperature, the pH value of the solution was adjusted to 10 with saturated aqueous sodium bicarbonate, diluted with DCM, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 170 mg (89%) of 3-[(3R)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]-2-hydroxypropanenitrile as a white solid. MS: m/z 280 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-368afd6c0b884e73a8d81643a30c9655
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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