Triethylamine → tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(1H-pyrrol-2-ylmethyl)amino]propylcarbamate

HRID 14318

반응식

HRID 14318 반응식
[NH2:1][CH2:2][C@@H:3]([OH:22])[C@@H:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([F:13])[CH:7]=1.[NH:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O.C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[F:12][C:10]1[CH:11]=[C:6]([CH:7]=[C:8]([F:13])[CH:9]=1)[CH2:5][C@H:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[C@H:3]([OH:22])[CH2:2][NH:1][CH2:28][C:24]1[NH:23][CH:27]=[CH:26][CH:25]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 13854Pyrrole-2-carboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 58802335tert-butyl (1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

생성물 1

HCID 86594202tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(1H-pyrrol-2-ylmethyl)amino]propylcarbamate수율 62%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

A mixture of tert-butyl (1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate (170 mg, 0.538 mmol), 1H-pyrrole-2-carbaldehyde (51 mg, 0.538 mmol), and triethylamine (60 mg, 0.592 mmol) was stirred in chloroform (10 mL) containing magnesium sulfate for 4 h. The reaction mixture was filtered and concentrated under reduced pressure. The resulting residue was dissolved in 2-propanol (10 mL) and sodium borohydride (26 mg, 0.699 mmol) was added. The reaction mixture was stirred overnight and then treated with methanol. The reaction mixture was concentrated under reduced pressure. Purification by flash column chromatography (silica, 9:1 chloroform/methanol) gave tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(1H-pyrrol-2-ylmethyl)amino]propylcarbamate (132 mg): 1H NMR (300 MHz, CD3OD) δ 6.82 (m, 4H), 6.21 (s, 1H), 6.09 (m, 1H), 4.09 (s, 2H), 3.66 (m, 2H), 3.19 (m, 1H), 3.13 (m, 1H), 3.03 (m, 1H), 2.88 (m, 1H), 1.31 (s, 9H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 2-propanol (10 mL)
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 9:1 chloroform/methanol)

출처 및 근거

ORD 기록
ord-10591fa1d71f44a894785a2384b0fe13
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

연결된 노트

불러오는 중…