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

HRID 488662노트

반응식

HRID 488662 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9b6992a029ca4c3eadb4348f818fcc09
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972340B2

반응 노트

불러오는 중…