Ammonium formate → HCID 71465770, 화합물

HRID 2201691노트

반응식

HRID 2201691 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:26])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([C:23](=[O:25])[CH3:24])[CH2:20]1)([O-])=O.C([O-])=O.[NH4+]>CO.C1COCC1.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:26])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([C:23](=[O:25])[CH3:24])[CH2:20]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 71007323(1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

생성물 1

HCID 71465770HCID 71465770, 화합물수율 22%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of (1-acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.15 g, 0.40 mmol, 1 eq.) in MeOH/THF (5 mL/5 mL) was added Zinc powder (0.13 g, 2.00 mmol, 5 eq.) and ammonium formate (0.20 g, 3.20 mmol, 8 eq.). The reaction was stirred at room temperature for 3 h. The reaction was filtered through Celite and the solids washed with MeOH. The filtrate was concentrated under reduced pressure then diluted with water. The obtained solid was filtered and dried. The crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to obtain (1-acetylazetidin-3-yl)methyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate (0.030 g, 22% yield). ESI+ MS: m/z 346 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 8.74 (bs, 1H), 7.50 (bs, 1H), 7.34 (d, J=5.0 Hz, 1H), 7.24-7.14 (m, 2H), 7.08-7.01 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 5.14 (bs, 2H), 4.30-4.10 (m, 3H), 3.95-3.80 (m, 2H), 3.68-3.55 (m, 1H), 2.95-2.85 (m 1H), 1.74 (s, 3H).

후처리

  1. filtrationThe reaction was filtered through Celite
  2. washthe solids washed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthen diluted with water
  5. filtrationThe obtained solid was filtered
  6. customdried
  7. customThe crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-a98d7b797a9140fa94299c46fe0e3b5d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365498B2

반응 노트

불러오는 중…