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[ CAS No. 100929-33-7 ] {[proInfo.proName]}

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Chemical Structure| 100929-33-7
Chemical Structure| 100929-33-7
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Product Details of [ 100929-33-7 ]

CAS No. :100929-33-7 MDL No. :MFCD09253729
Formula : C9H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OZNSMUSCZYUFHD-VIFPVBQESA-N
M.W : 167.21 Pubchem ID :10866717
Synonyms :

Safety of [ 100929-33-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100929-33-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 100929-33-7 ]

[ 100929-33-7 ] Synthesis Path-Downstream   1~81

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YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; In sodium hydroxide; hydrochloric methanol; The process is performed under the conditions of Example 2, starting with 12.45 g of tert-butyl (1R)-1-(4-methoxyphenyl) -2-hydroxyethylcarbamate in 130 cm3 of 2.5 N hydrochloric methanol, with stirring for 1 h 30 minutes at a temperature in the region of 20 C., and then for 30 minutes at a temperature in the region of 30 C. The reaction mass is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40 C. 61 cm3 of aqueous 5% sodium hydrogen carbonate solution are added to the residue obtained and the mixture is then extracted with 3 times 100 cm3 of dichloromethane. The aqueous phase is separated out after settling has taken place and is then evaporated as above. The solid obtained is taken up in 65 cm3 of aqueous 1 N sodium hydroxide solution and the resulting solution is reduced to 2/3 of its volume by concentration under the above conditions. The mixture is extracted with 3 times 100 cm3 of dichloromethane. The extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure (5 kPa) at a temperature in the region of 40 C. The crystals obtained are dried under reduced pressure (5 kPa) at about 20 C. 5.86 g of (2R)-2-amino-2-(4-methoxyphenyl) -1-ethanol are obtained in the form of a white solid melting at 103 C. tert-Butyl (1R)-1-(4-methoxyphenyl)-2-hydroxyethylcarbamate:
YieldReaction ConditionsOperation in experiment
52.71% With lithium aluminium tetrahydride; In diethyl ether; for 3.0h;Reflux; General procedure: Cryohydrate under bath, 2 - hydroxy -1 - phenyl ethyl oxime (4g, 26.5mmol) soluble in an amount of 40 ml anhydrous ethyl ether, is dropped into the containing lithium aluminum hydride (2.51g, 66 . 2mmol) ethyl ether suspension of 10 ml, then completing 30min, gradually heating to reflux, the reaction 3h. To be after the reaction is complete, under the ice salt bath, is dropped into the aqueous ether 2.5 ml, stirring 30min, then one by one 15% sodium hydroxide solution with 2.5 ml, continuing to stir 30min, add 7.5 ml water, stirring 1h, adding anhydrous magnesium sulfate, stirring 1h. Filtering, and for 20 ml of ethyl ether run filter washing cake. Drying of the organic layer with anhydrous magnesium sulfate, desolvation, yellow oily product obtained 0.58g, yield: 15.98%.
  • 7
  • [ 57056-39-0 ]
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  • C34H37N3O6 [ No CAS ]
  • 8
  • [ 50-00-0 ]
  • [ 100929-33-7 ]
  • (R)-4-(4-Methoxy-phenyl)-oxazolidine [ No CAS ]
  • (5R,10R)-5,10-bis(4-methoxyphenyl)-1,6-diaza-3,8-dioxabicyclo[4.4.1]undecane [ No CAS ]
  • C21H26N2O4 [ No CAS ]
  • 9
  • [ 139152-08-2 ]
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  • (R,R)-1,2-dichloro-4,5-bis(4-(p-methoxyphenyl)oxazolin-2-yl)benzene [ No CAS ]
  • 10
  • [ 100929-33-7 ]
  • [ 5659-93-8 ]
  • 2,2-bis[2-[4-(4-methoxyphenyl)-1,3-oxazolinyl]]propane [ No CAS ]
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  • [ 637-69-4 ]
  • diazotized 4-amino-benzonitrile [ No CAS ]
  • [ 100929-33-7 ]
  • 12
  • [ 100929-33-7 ]
  • (1S)-N-methyl-1-(4-methoxyphenyl)-2-(isoindolin-2-yl)ethylamine [ No CAS ]
  • 13
  • [ 100929-33-7 ]
  • C17H18NO(1+)*Cl(1-) [ No CAS ]
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  • [ 100929-27-9 ]
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  • [ 100929-33-7 ]
  • 3-Hydroxy-N-[(R)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-3-phenyl-propionamide [ No CAS ]
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  • 22
  • [ 590-42-1 ]
  • [ 100929-33-7 ]
  • N-(tert-butyl)-N'-[(1R)-1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; ethanol; water; The process is performed under the conditions of Example 1, starting with 5.78 g of <strong>[100929-33-7](2R)-2-amino-2-(4-methoxyphenyl)-1-ethanol</strong> and 6.48 cm3 of tert-butyl isothiocyanate in 73 cm3 of ethanol for 17 h 30 minutes at a temperature in the region of 20 C. The reaction mass is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40 C. and the solid residue obtained is then ground in 45 cm3 of water, filtered and washed with twice 20 cm3 of water and twice 25 cm3 of diethyl ether. The crystals are dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 45 C. 4.9 g of N-(tert-butyl)-N'-[(1R)-1-(4-methoxyphenyl)2-hydroxyethyl]-thiourea are obtained in the form of a white solid. (Rf=0.60 in ethyl acetate, on a Merck 60F254R silica plate). (2R)-2-Amino-2-(4-methoxyphenyl)-1-ethanol:
  • 23
  • [ 590-42-1 ]
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  • N-(tert-butyl)-N'-[1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; ethanol; water; N-(tert-Butyl)-N'-[1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea: The process is performed under the conditions of Example 1, starting with 1.3 g of 2-amino -2-(4-methoxyphenyl)-1-ethanol and 1.46 cm3 of tert-butyl isothiocyanate in 12 cm3 of absolute ethanol for 21 hours at a temperature in the region of 20 C. After concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40 C., the residue obtained is taken up in 10 cm3 of water. A crystalline precipitate forms, which is filtered off, washed with 3 times 5 cm3 of diethyl ether and dried under reduced pressure (10 Pa) at a temperature in the region of 40 C. 1.32 g of N-(tert-butyl) -N'-[1- (4-methoxyphenyl)-2-hydroxyethyl]thiourea are obtained in the form of a white solid melting at 127 C. 2-Amino-2-(4-methoxyphenyl)-1-ethanol:
  • 24
  • tert-butyl 1-(4-methoxyphenyl)-2-hydroxyethylcarbamate [ No CAS ]
  • [ 100929-33-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In methanol; sodium hydroxide; sodium bicarbonate; A mixture of 3.4 g of tert-butyl 1-(4-methoxyphenyl)-2-hydroxyethylcarbamate in 32 cm3 of methanol containing 10% by mass of anhydrous hydrogen chloride is stirred for 1 hour at a temperature in the region of 20 C. The reaction medium is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40 C. The residue is taken up in 9 cm3 of aqueous 5% sodium hydrogen carbonate solution and the mixture is then extracted with 3 times 30 cm3 of dichloromethane. The aqueous phase is concentrated as above and the white solid obtained is then taken up in 17 cm3 of aqueous 1 N sodium hydroxide solution. The precipitate is extracted with 3 times 30 cm3 of dichloromethane. The combined organic extracts are evaporated under reduced pressure (5 kPa) at a temperature in the region of 40 C. The white solid obtained is dried under reduced pressure (10 Pa) at a temperature in the region of 40 C. 1.3 g of 2-amino-2-(4-methoxyphenyl)-1-ethanol are obtained in the form of a white solid melting at 96 C. tert-Butyl 1-(4-methoxyphenyl)-2-hydroxyethylcarbamate:
  • 25
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  • [ 67-64-1 ]
  • C12H17NO2 [ No CAS ]
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  • [ 1286280-54-3 ]
YieldReaction ConditionsOperation in experiment
43% With N-ethyl-N,N-diisopropylamine; In dichloromethane; A solution of (lS,2S)-2-thiophen-2-yl-cyclopropanecarbonyl chloride (0.78 mmol in 3 ml of DCM, generated as in Example 6) was added to a solution of (R)-2- amino-2-(4-methoxy-phenyl)-ethanol (130.3 mg, 0.78 mmol) in DCM (3 mL), followed by DIEA (277.2 uL, 1.56 mmol). The reaction was quenched withH20/EtOAc and work up. The organic layer was dried (MgS04) and the solvent was removed. The residue was subjected to flash column to afford the titled compound (105 mg, 43%).
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  • 45
  • [ 199392-93-3 ]
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YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium on carbon; In methanol; under 760.051 Torr; for 1.5h; A mixture of [(R)-2-Hydroxy-l-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester (761 mg, 2.53 mmol) and Pd/C (76 mg) in MeOH (8 mL) was stirred under H2 (1 atm) for 1.5 h. The mixture was filtered and the filtrate was concentrated to give the titled compound (432 mg, 100%).
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 1551.49 Torr; for 12h; A mixture of (R)-N-(benzyloxycarbonyl)-4-methoxyphenylglycinol 19 (0.32g, 1.06mmol) and palladium on carbon (10%, 0.18g) in methanol (15mL) was shaken under hydrogen at 30psi for 12h at room temperature. The crude reaction mixture was filtered through a short column of silica gel using ethyl acetate as eluent to remove the hydrogenation catalyst. Concentration of the solution gave the crude alcohol 14 (0.11g, 61%) as an off-white solid, mp 96-98C; [alpha]18D=-38.5[alpha]D18=-38.5 (c 0.46, CHCl3), {Lit.,27 [alpha]18D[alpha]D18 (for the (S)-enantiomer)=+38.3 (c 0.43, CHCl3)}; numax/cm-1 (KBr) 3348 br, 3287, 2894-2837, 1615, 1518; deltaH (300MHz) 2.05 (3H, br s, NH2, OH), 3.53 [1H, dd, A of ABX, JAB 10.7, JAX 8.4, one of C(1)H2], 3.70 [1H, dd, B of ABX, JAB 10.6, JBX 4.4, one of C(1)H2], 3.80 (3H, s, OCH3), 3.95-4.07 [1H, bm, X of ABX, C(2)H], 6.86-6.92 (2H, m, aromatic H), 7.22-7.28 (2H, m, aromatic H).
  • 46
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  • 4-(4-methoxyphenyl)-4,5-dihydro-1,3-thiazol-2-ylamine [ No CAS ]
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  • [ 2540-53-6 ]
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  • [ 100929-33-7 ]
  • C19H27NO3SSi [ No CAS ]
  • C19H27NO3SSi [ No CAS ]
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  • [ 98-01-1 ]
  • [ 6372-02-7 ]
  • [ 88333-03-3 ]
  • [ 100929-33-7 ]
  • (3S,3aR,6R,7R,7aR)-N-benzyl-2-((R)-2-hydroxy-1-(4-methoxyphenyl)ethyl)-7-iodo-1-oxo-1,2,3,6,7,7ahexahydro-3a,6-epoxyisoindole-3-carboxamide [ No CAS ]
  • (3S,3aR,6S,7R,7aR)-N-benzyl-2-((R)-2-hydroxy-1-(4-methoxyphenyl)ethyl)-7-iodo-1-oxo-1,2,3,6,7,7ahexahydro-3a,6-epoxyisoindole-3-carboxamide [ No CAS ]
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  • [ 100-52-7 ]
  • [ 100929-33-7 ]
  • C22H27NO5 [ No CAS ]
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  • [ 64-18-6 ]
  • [ 771468-94-1 ]
  • [ 100-52-7 ]
  • [ 100929-33-7 ]
  • C22H28N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In methanol; at 20℃; for 40h; General procedure: To a stirred solution of aldehyde (0.0980 mmol) in methanol(0.5 mL) at r.t., were added amine (0.0650 mmol),carboxylic acid (0.0650 mmol), and HMPI (1, 9.0 mg, 0.091mmol). After stirring at r.t. for 40 h, the mixture wasconcentrated under reduced pressure. The residue wasdissolved in CHCl3 (1 mL) and washed successively withsat. aq Na2CO3 (1 mL), sat. aq NH4Cl (1 mL), and brine (1mL). The organic layer was dried over Na2SO4 andconcentrated under reduced pressure. The residue waspurified by column chromatography on silica gel (1 g;hexane-EtOAc) to give the Ugi product X.
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  • [ 23020-15-7 ]
  • [ 100929-33-7 ]
  • [ 1531592-38-7 ]
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  • [ 1531592-44-5 ]
  • [ 100929-33-7 ]
  • [ 1531592-41-2 ]
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  • [ 1417656-40-6 ]
  • [ 100929-33-7 ]
  • [ 1531592-42-3 ]
  • 56
  • [ 100929-33-7 ]
  • (+)-(1S,2S)-2-(4-fluorophenyl)cyclopropanecarboxylic acid [ No CAS ]
  • [ 1531592-43-4 ]
  • 57
  • C19H35NO3SSi [ No CAS ]
  • [ 100929-33-7 ]
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  • [ 57591-61-4 ]
  • [ 100929-33-7 ]
  • 59
  • [ 213136-30-2 ]
  • [ 100929-33-7 ]
  • 60
  • (R)-N-(benzyloxycarbonyl)-2-(4-methoxyphenyl)glycine methyl ester [ No CAS ]
  • [ 100929-33-7 ]
  • 61
  • [ 100929-33-7 ]
  • [ 5659-93-8 ]
  • [ 1487433-91-9 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In dichloromethane; at 0℃; for 0.666667h;Inert atmosphere; General procedure: Dimethylmalonyl chloride (0.50g, 2.92mmol), in DCM (3mL) was added dropwise to a heterogeneous solution of (R)-2-amino-2-(4-chlorophenyl)ethanol 9 (1.00g, 5.83mmol) and triethylamine (2.0mL, 14.6mmol) in DCM (6mL) at 0C. The homogeneous reaction mixture was removed from the bath and stirred for 40min. Aqueous hydrochloric acid (10%, 10mL) was added to the reaction mixture and the biphasic mixture was stirred for 15min. The layers were separated and the aqueous layer was washed with DCM (2×10mL). The combined organic layer was washed with saturated aqueous sodium bicarbonate (15mL). The aqueous layer was back extracted with DCM (2×10mL). The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the bisamide 20 as a pale yellow solid. Purification by recrystallisation from a mixture of DCM and hexane gave the pure bisamide 20 (0.96g, 73%) as a white solid
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  • [ 159848-74-5 ]
YieldReaction ConditionsOperation in experiment
78 mg With triethylamine; In tetrahydrofuran; at 20℃; General procedure: To a solution of the 1,2-amino alcohols (0.5mmol) in THF (3mL) was added (Boc)2O (163.7mg, 0.75mmol) and Et3N (126.5mg, 1.25mmol). The reaction was stirred at room temperature for about 1-2h until the TLC analysis showed that the reaction was complete. The mixture was concentrated under vacuum and purified by preparative TLC to afford the desired products.
  • 63
  • [ 2632-13-5 ]
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  • 64
  • (S)-1-bromo-2-hydroxy-2-(p-methoxyphenyl)ethane [ No CAS ]
  • [ 100929-33-7 ]
  • 65
  • (S)-2-(4-methoxyphenyl)oxirane [ No CAS ]
  • [ 100929-33-7 ]
  • 66
  • (R)-2-azido-2-(4-methoxyphenyl)ethan-1-ol [ No CAS ]
  • [ 100929-33-7 ]
YieldReaction ConditionsOperation in experiment
0.172 g With water; triphenylphosphine; In tetrahydrofuran; at 70℃; General procedure: To a solution of 1,2-azido alcohol 5 (1mmol) in THF (5mL) was added triphenylphosphine (393mg, 1.5mmol) and water (360mg, 20mmol). The mixture was heated at 70C for 1-2h until TLC analysis showed that the reaction was complete. Next, the mixture was concentrated under vacuum and purified by preparative TLC to afford the desired product.
  • 67
  • [ 1265176-52-0 ]
  • [ 100929-33-7 ]
  • 1-(2-hydroxy-1-(4-methoxyphenyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In tetrahydrofuran; at 20 - 24℃; To 3-(4-isothiocyanato-phenyl)-l-(4-trifluoromethoxy-phenyl)-lH-l,2,4-triazole (1.09 g, 2.70 mmol) in tetrahydrofuran (7 mL) was added 2-amino-2-(4- methoxyphenyl)ethanol (0.506 g, 3.30 mmol) (Reggelin, M. et al., Synlett, 2012, 23, 1095-1098). The reaction was stirred overnight at room temperature. The reaction mixture was concentrated and the residue was recrystallized with petroleum ether providing the title compound as a white solid (1.42 g, 81%): *H NMR (300 MHz, CDCI3) delta 7.96 (s, 1H), 7.72 - 7.57 (m, 2H), 7.27 (s, 1H), 7.23 - 7.14 (m, 2H), 6.87 - 6.72 (m, 4H), 6.64 - 6.56 (m, 2H), 6.38 - 6.22 (m, 3H), 5.05 (s, 1H), 3.47 - 3.28 (m, 2H), 3.20 (s, 3H); ESIMS m/z 530 ([M + H]+).
  • 68
  • [ 1265176-52-0 ]
  • [ 100929-33-7 ]
  • 4-(4-methoxyphenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine [ No CAS ]
  • 69
  • (R)-isopropyl 2-(4-methoxyphenyl)-2-[(S)-1,1-dimethylethylsulfinamido]acetate [ No CAS ]
  • [ 100929-33-7 ]
  • 70
  • (R)-2-isopropoxy-1-(4-methoxyphenyl)-2-oxoethan-1-aminium chloride [ No CAS ]
  • [ 100929-33-7 ]
  • 71
  • [ 101128-44-3 ]
  • [ 100929-33-7 ]
  • 72
  • (S,Z)-isopropyl 2-[(tert-butylsulfinyl)imino]-2-(4-methoxyphenyl)acetate [ No CAS ]
  • [ 100929-33-7 ]
  • 73
  • 4-methoxyphenethyl 2,2,2-trichloroacetimidate [ No CAS ]
  • [ 100929-33-7 ]
  • 76
  • [ 100929-33-7 ]
  • [ 104-94-9 ]
  • [ 1624-46-0 ]
YieldReaction ConditionsOperation in experiment
77%Spectr. With 2,6-Di-tert-butyl-1,4-benzoquinone; oxygen; In ethanol; at 70℃; for 24.0h; General procedure: To a solution of 2,6-di-tert-butyl-1,4-benzoquinone (2c, 0.20 mmol, 44 mg, 0.2 equiv) and p-anisidine (6a, 2.0 mmol, 246 mg, 2.0 equiv) in ethanol (3.2 mL) was added the 1,2-amino alcohol 1 (1.0 mmol). The flask was purged with O2 and then heated to 70 C with vigorous stirring for 24 h. After the reaction mixture was cooled to room temperature, benzyl ether (1.0 mmol, 190 muL, 1.0 equiv) was added as an internal standard and the reaction was concentrated under reduced pressure. 1H NMR was taken in CDCl3 and the spectrum obtained was used to assess the yield of imine 7. The desired imine product was subsequently purified by flash chromatography on triethylamine treated silica gel (eluent: 10% ethyl acetate in hexanes) to enable characterization of the imine product 7 through 1H NMR, 13C NMR, IR and MS.
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  • [ 123-11-5 ]
  • [ 100929-33-7 ]
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  • [ 6388-72-3 ]
  • [ 100929-33-7 ]
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  • [ 144924-02-7 ]
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  • [ 50-00-0 ]
  • [ 100929-33-7 ]
  • N,N-Dimethyl-4-methoxy-β-hydroxyphenethylamin [ No CAS ]
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