4-Methylmorpholine → (S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1678502노트

반응식

HRID 1678502 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]([F:21])([F:20])[F:19])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[C:22]([O:26][C:27]([N:29]1[CH2:32][CH2:31][C@H:30]1[C:33]([OH:35])=O)=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=N[C:46]2C=CC=C[C:45]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:32][CH2:31][C@H:30]1[C:33](=[O:35])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:45][CH3:46])=[O:15])=[CH:12][CH:13]=2)[C:5]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:4][CH:3]=1)=[O:28])([CH3:23])([CH3:24])[CH3:25]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acidHCID 673729305'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid

생성물 1

HCID 67371803(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester수율 78.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5′-amino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid (150 mg), (S)-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester (93 mg), HBTU (262 mg) and N-methyl morpholine (0.14 ml) in dry DMF (3 ml) was stirred at room temp for 18 h. The mixture was then partitioned between water and DCM. The dried organic layer was evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol 1:1 gave a pale orange oil (185 mg).

후처리

  1. customThe mixture was then partitioned between water and DCM
  2. customThe dried organic layer was evaporated
  3. customthe residue purified on silica gel
  4. washElution with ethyl acetate:petrol 1:1

출처 및 근거

ORD 기록
ord-65f520f383b24dc4a74c1939a07159ab
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008303B2

반응 노트

불러오는 중…