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 1582366노트

반응식

HRID 1582366 반응식
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]

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 54183720HCID 54183720, 화합물

생성물 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-one수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매3회

실험 절차

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%). NMR (400 MHz, DMSO-d6/CD3COOD) δ: 2.41 (m overlapping DMSO, 2H); 3.45 (m, 1H); 3.54 (m, 1H); 3.48 (overlapping m, 4H); 3.82 (dd, 1H); 4.08-4.25 (m, 3H); 4.39 (m, 1H); 4.92 (m, 1H); 6.01 (s, 1H); 7.27 (dd, 1H); 7.32 (t, 1H); 7.45 (dd, 1H); 8.01 (s, 1H); 2×OH, 1×NH missing, exchanged. MS (ESP): 464 (MH+) for C20H22FN5O2S

후처리

  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

출처 및 근거

ORD 기록
ord-843ca9d7bfdf4951abebedc2a81b343b
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

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