Ammonia → 3-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)-5(S)-(1,2,5-thiadiazol-3-ylaminomethyl)oxazolidin-2-one

HRID 8183Notes

Reaction equation

HRID 8183 reaction equation
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][C@H:24]([CH2:26][N:27]([C:35]5[CH:39]=[N:38][S:37][N:36]=5)C(OC(C)(C)C)=O)[O:23][C:22]4=[O:40])=[CH:17][C:16]=3[F:41])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.N.C(OCC)C>FC(F)(F)C(O)=O.O>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:35]4[CH:39]=[N:38][S:37][N:36]=4)[O:23][C:22]3=[O:40])=[CH:17][C:16]=2[F:41])=[CH:11][CH2:10]1)=[O:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 54183720HCID 54183720, compound

Product 1

HCID 695847513-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)-5(S)-(1,2,5-thiadiazol-3-ylaminomethyl)oxazolidin-2-oneYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent3×

Procedure

A solution of 3-(4(1-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)-1,2,5-thiadiazol-3-ylamino-methyl)oxazolidin-2-one (580 mg, 0.96 mM) in trifluoroacetic acid (2 ml) was warmed at 60° for 2 minutes and then kept at ambient temperature for 10 minutes. A solution of trifluoroacetic acid in water (10 ml, 1:1) was added and the mixture kept for 30 minutes. More trifluoroacetic acid (2 ml) was added and after a further 90 minutes, excess aqueous ammonia was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water, sodium bicarbonate solution and brine and dried (sodium sulfate). Solvent was evaporated and the residue purified on a silica Mega Bond Elut® column, eluting with dichloromethane and then 4% methanol in dichloromethane to give an oil which solidified on trituration with diethyl ether to give the title product (203 mg, 46%).

Workup

  1. waitthe mixture kept for 30 minutes
  2. extractionthe mixture extracted three times with ethyl acetate
  3. washThe combined extracts were washed with water, sodium bicarbonate solution and brine
  4. dry with materialdried (sodium sulfate)
  5. customSolvent was evaporated
  6. customthe residue purified on a silica Mega Bond Elut® column
  7. washeluting with dichloromethane
  8. custom4% methanol in dichloromethane to give an oil which

Sources & evidence

ORD record
ord-113e2b98e3cf49ecb1df7262ef21fec9
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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