Diisopropylethylamine → Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoate

HRID 488662ノート

反応式

HRID 488662 の反応式
N[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10].[C:18]([NH:21][C@H:22]([C:67]([OH:69])=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)(=[O:20])[CH3:19].F[B-](F)(F)F.[N:75]1(OC(N(C)C)=[N+](C)C)[C:79]2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:18]([NH:21][CH:22]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)[C:67]([NH:75][CH2:79][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:69])(=[O:20])[CH3:19]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11832643Methyl 2-(4-aminobutoxy)-6-hydroxybenzoateHCID 69803959N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine

生成物 1

HCID 22271917Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoate収率 57.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate (42 mg, 0.12 mmol), N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine (70 mg, 0.1 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (32 mg, 0.1 mmol) and diisopropylethylamine (70 μL, 0.4 mmol) in N,N-dimethylformamide (1 mL) was stirred at ambient temperature overnight, diluted with ethyl acetate and washed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL), dried (MgSO4), filtered and concentrate under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide of titled compound 54 mg.

後処理

  1. washwashed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrate under reduced pressure
  5. customThe residue was purified on silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-9b6992a029ca4c3eadb4348f818fcc09
出典データセット
uspto-grants-2005_12
特許番号
US06972340B2

反応ノート

読み込み中…