Triethylamine → Ammonia

HRID 2393642노트

반응식

HRID 2393642 반응식
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10].Cl.[NH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C([N:36](CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[C:19]([O:18][C:16]([NH:1][C@@H:2]([C:13]([NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:12])=[N:8][N+:9]([O-:11])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20].[NH3:36]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 66449Tyramine hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178454201HCID 178454201, 화합물

생성물 2

HCID 222AmmoniaHCID 136381088HCID 136381088, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 1.0 g (3.13 Mol) of Boc-D-Arg(NO2)-OH, 0.57 g (3.28 mMol) of tyramine-hydrochloride, 0.91 ml (0.66 g=6.53 mMol) of triethylamine and 20 ml of anhydrous acetonitrile were added 1.05 g (3.27 mMol) of TBTU, with stirring and external cooling with ice water. The mixture was allowed to come up to ambient temperature and stirring was continued overnight under these conditions. The precipitate was filtered off, the filtrate was evaporated down in vacuo, the residue was distributed between water and ethyl acetate. The ethyl acetate phase was then purified by column chromatography on silica gel (Macherey-Nagel, 35-70 mesh ASTM) using dichloromethane/methanol/cyclohexane/conc. aqueous ammonia=68/15/15/2 (v/v/v/v). 0.8 g (58% of theory) of the title compound were obtained in the form of an amorphous foam, Rf 0.49 (Macherey-Nagel Polygram® SIL G/UV254, ready-made films for TLC; eluant: dichloromethane/methanol/cyclohexane/conc. aqueous ammonia=68/15/15/2 (v/v/v/v)).

후처리

  1. customto come up to ambient temperature
  2. stirringstirring
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate was evaporated down in vacuo
  5. customThe ethyl acetate phase was then purified by column chromatography on silica gel (Macherey-Nagel, 35-70 mesh ASTM)

출처 및 근거

ORD 기록
ord-56da4ee754a44ac7b66c2097e768639a
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807875

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