2-Propanol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)- (9CI) → (S)-1-(2-((1-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one

HRID 633448Notes

Reaction equation

HRID 633448 reaction equation
ClC1C=C(NC2N=C(N[C@@H]3C[C@H]4N(CCC4)C(C)(C)C3)C(F)=CN=2)C=CC=1OCCO.F[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[N:42]1[C:46](=[O:47])[N:45]([CH3:48])[N:44]=[N:43]1.CC(C)([O-])C.[K+].[Si:55]([O:62][CH2:63][C@@H:64]([OH:66])[CH3:65])([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56]>C1COCC1>[Si:55]([O:62][CH2:63][C@@H:64]([O:66][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[N:42]1[C:46](=[O:47])[N:45]([CH3:48])[N:44]=[N:43]1)[CH3:65])([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 131751362-Propanol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)- (9CI)HCID 23665647Potassium tert-butoxideHCID 582871741-(2-fluoro-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-oneHCID 718112862-(2-chloro-4-((4-(((7R,8aS)-5,5-dimethyloctahydroindolizin-7-yl)amino)-5-fluoropyrimidin-2-yl)amino)phenoxy)ethan-1-ol

Product 1

HCID 86704539(S)-1-(2-((1-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A similar procedure as detailed above for Compound 133 was used. 1-(2-fluoro-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one (prepared according to US patent application 20110130415) (239 mg, 1.0 mmol), potassium tert-butoxide (146 mg, 1.2 mmol) and (S)-1-((tert-butyldimethylsilyl)oxy)propan-2-ol (Milestone PharmaTech) (209 mg, 1.1 mmol) in THF (10 mL) was stirred for 2 hr at room temperature to give the product after workup (yield assumed quantitative=410 mg). The product was used in the next step without further purification.

Workup

  1. customto give the product
  2. customafter workup (yield assumed quantitative=410 mg)
  3. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-1220608ed181424c990594f33263b084
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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