1-Hydroxybenzotriazole → HCID 19094385, 화합물

HRID 466232노트

반응식

HRID 466232 반응식
[CH3:1][O:2][P:3]([CH2:7][NH:8][CH:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])([O:5][CH3:6])=[O:4].[CH2:31]([O:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]O)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:1][O:2][P:3]([CH2:7][NH:8][CH:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][NH:41][C:39]([O:38][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:40])=[O:16])=[O:11])([O:5][CH3:6])=[O:4]

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 40724145-(Z-Amino)-1-pentanolHCID 76083370HCID 76083370, 화합물

생성물 1

HCID 19094385HCID 19094385, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

The compound of example 12(g) is prepared as follows: N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid (700 mg; 1.61 mmol) in dimethyl formamide (DMF) (10 ml) is treated sequentially with N-benzyloxycarbonyl-5-aminopentanol (400 mg; 1.98 mmol) in DMF (2 ml), 1-hydroxybenzotriazole (HOBT) (265 mg; 1.96 mmol), 4-N,N-dimethylaminopyridine (DMAP) (239 mg; 1.96 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) (553 mg; 3.22 mmol). The mixture is stirred for 20 hours, then partitioned between ethyl acetate (50 ml) and 1N HCl(30 ml). The organic layer is washed with a saturated solution of sodium bicarbonate (30 ml), then with brine (30 ml) before being dried over anhydrous sodium sulfate. After concentration under reduced pressure, the oily residue is purified by column chromatography on silica gel, eluting first with ethyl acetate, then with 5% methanol in methylene chloride to yield N-benzyloxycarbonyl-5-aminopentyl N-[2-(dimethylphosphonomethyl amino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate as an oil; Rf(SiO2 ; MeOH/CH2Cl2):0.4.

후처리

  1. custompartitioned between ethyl acetate (50 ml) and 1N HCl(30 ml)
  2. washThe organic layer is washed with a saturated solution of sodium bicarbonate (30 ml)
  3. dry with materialwith brine (30 ml) before being dried over anhydrous sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe oily residue is purified by column chromatography on silica gel
  6. washeluting first with ethyl acetate

출처 및 근거

ORD 기록
ord-0e607a9af4414bfaa4ea3ad8b58b14fc
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155100

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