Benzyl Alcohol → HCID 123524169, compound

HRID 2203668Notes

Reaction equation

HRID 2203668 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[N:29]([CH:30]([CH3:32])[CH3:31])[N:28]=[C:27](C(O)=O)[CH:26]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:39]([CH:42](C)C)CC)(C)C.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:54]C1C=CC=CC=1>C1(C)C=CC=CC=1>[Si:1]([O:18][CH:19]1[CH2:20][CH:21]2[CH:23]([CH:22]2[C:25]2[N:29]([CH:30]([CH3:32])[CH3:31])[N:28]=[C:27]([NH:39][C:42](=[O:54])[O:52][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:26]=2)[CH2:24]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 123222247HCID 123222247, compound

Product 1

HCID 123524169HCID 123524169, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 500 mL three-neck flask was charged with 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazole-3-carboxylic acid (26 g, 53 mmol), diisopropylethylamine (14 mL, 0.080 mol), benzyl alcohol (17.26 g, 159.6 mmol) and anhydrous toluene (300 mL). The reaction mixture was purged with nitrogen for 2 min and heated to 100° C. Diphenyl phosphorazidate (17.2 mL, 79.85 mmol) was added dropwise to the reaction mixture, and the reaction was maintained at 100° C. After 16 h, the reaction mixture was concentrated in vacuo. The resulting residue was purified by flash column chromatography (20:1 petroleum ether/ethyl acetate) to afford benzyl (5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazol-3-yl)carbamate as a yellow oil (28 g, 89%). LRMS: [M+H]+ 594.0.

Workup

  1. customThe reaction mixture was purged with nitrogen for 2 min
  2. temperaturethe reaction was maintained at 100° C
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe resulting residue was purified by flash column chromatography (20:1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-7cc44654aa8640f39ec5d4bf5273fddc
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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