Triethylamine → HCID 178444654, 화합물

HRID 1088614노트

반응식

HRID 1088614 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=O)[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C@H:20]([C@@H:28]([OH:34])[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([NH:19][C@H:20]([C@@H:28]([OH:34])[CH2:29][CH2:30][CH:31]([CH3:32])[CH3:33])[CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:18])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 14671722HCID 14671722, 화합물HCID 178454169HCID 178454169, 화합물

생성물 1

HCID 178444654HCID 178444654, 화합물수율 63.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of N-t-butoxycarbonyl-L-histidine (363 mg) and 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (294 mg) in dry N,N-dimethylformamide (30 ml) which was cooled to 0° C., were added a solution of diphenyl phosphorylazide (390 mg) in dry N,N-dimethylformamide (5 ml)and triethylamine (144 mg). The mixture was stirred overnight at ambient temperature. After evaporation of the solvent, the residue was dissolved in ethyl acetate (30 ml) and the solution was washed with 10% citric acid solution, saturated sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (chloroform as eluent) to give 2(S)-(N-t-butoxycarbonyl-L-histidyl)amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (384 mg) as an amorphous powder.

후처리

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. washthe solution was washed with 10% citric acid solution, saturated sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (chloroform as eluent)

출처 및 근거

ORD 기록
ord-8933efa28b4d43e8b3007c54577d1695
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963530

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