Trifluoroacetic acid → HCID 21978406, 화합물

HRID 10232노트

반응식

HRID 10232 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[S:6]([CH2:9][CH:10]1[CH2:13][N:12]([C:14](OC(C)(C)C)=O)[CH2:11]1)(=[O:8])=[O:7].C(O)(C(F)(F)F)=O.[BH3-]C#N.[Na+].[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[C:34](C=O)=[N:33]1>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[S:6]([CH2:9][CH:10]1[CH2:11][N:12]([CH2:14][C:34]2[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[S:32][N:33]=2)[CH2:13]1)(=[O:7])=[O:8]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 1260711973437-27-1HCID 21978417HCID 21978417, 화합물

생성물 1

HCID 21978406HCID 21978406, 화합물수율 32.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 3-[(1,3-thiazol-2-ylsulfonyl)methyl]azetidine-1-carboxylate (51 mg, 0.16 mmol) was dissolved in DCM (0.5 mL) and TFA (0.5 mL) was added. The resulting mixture was stirred for 30 min. then concentrated in vacuo. The residual oil was taken up in MeOH (2 mL), then NaCNBH3 (16.2 mg, 0.26 mmol) and 1,2-benzisothiazole-3-carbaldehyde (28.6 mg, 0.18 mmol) [prepared by the method of T. Hasegawa, Y. Akiyama, T. Imai, E. Sato, Y. Yamamoto, J. Tanaka, H. Nagaso, K. Fuji, K. Murase, M. Shiiyama, WO 98/08816] were added. The mixture was stirred overnight then partitioned between 0.5 N NaOH (20 mL) and EtOAc (20 mL). The aqueous phase was washed with EtOAc (20 mL) and the organic layers were combined, washed with saturated brine (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified using column chromatography, on silica gel, eluting with 50–60% EtOAc in DCM to give the title compound as a colourless oil (19 mg, 29%). 1H NMR (400 MHz, CDCl3) δ 2.96–3.06 (1H, m), 3.12 (2H, m), 3.57 (2H, t, J=7.6 Hz), 3.72 (2H, d, J=7.3 Hz), 4.04 (2H, s), 7.41–7.45 (1H, m), 7.50–7.54 (1H, m), 7.74 (1H, d, J=3.1 Hz), 7.91 (1H, d, J=8.2 Hz), 8.05 (1H, d, J=3.0 Hz), 8.10 (1H, d, J=8.1 Hz). m/z (ES+) 366 (M+H)+.

후처리

  1. concentrationthen concentrated in vacuo
  2. additionShiiyama, WO 98/08816] were added
  3. stirringThe mixture was stirred overnight
  4. customthen partitioned between 0.5 N NaOH (20 mL) and EtOAc (20 mL)
  5. washThe aqueous phase was washed with EtOAc (20 mL)
  6. washwashed with saturated brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. washon silica gel, eluting with 50–60% EtOAc in DCM

출처 및 근거

ORD 기록
ord-eab3cf5bbfa84edebeddc16063e41490
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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