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

HRID 1678502ノート

反応式

HRID 1678502 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-65f520f383b24dc4a74c1939a07159ab
出典データセット
uspto-grants-2011_08
特許番号
US08008303B2

反応ノート

読み込み中…