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Ethyl Acetate → 2-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester

HRID 899047
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HRID 899047 반응식
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]([NH:15][CH:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]([NH:19][CH:20]([P:24](=[O:27])([OH:26])[OH:25])[CH:21]([CH3:23])[CH3:22])=[O:18])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:35][O:36][C:37](=[O:51])[CH:38](O)[CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C(OCC)(=O)C>CN(C=O)C>[CH3:35][O:36][C:37](=[O:51])[CH:38]([O:27][P:24]([CH:20]([NH:19][C:17](=[O:18])[CH:16]([NH:15][C:13]([O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:14])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH:21]([CH3:22])[CH3:23])([OH:26])=[O:25])[CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 543300255-Tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl esterHCID 54345348[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-phosphonic acid

생성물 1

HCID 570512352-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester
수율 66.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
-5 °C

실험 절차

Thionyl chloride (49 μL, 0.67 mmol) was added dropwise to a solution of [1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-phosphonic acid (208 mg, 0.48 mmol) in DMF (5 mL) at −20° C. under argon. The mixture was stirred for 35 min at −5° C. A solution of 5-tert-Butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester (166 mg, 0.67 mmol) in DMF (1 mL) was added and the mixture was stirred for 90 min at room temperature. Ethyl acetate was added and the mixture was washed with 1 M HCl, dried and concentrated under reduced pressure. The crude product was purified using chromathography (CHCl3/MeOH/H2O, 10:1:0→10:5:1) to give 2-{[1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (211 mg, 66%).

후처리

  1. stirringthe mixture was stirred for 90 min at room temperature
  2. washthe mixture was washed with 1 M HCl
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified

출처 및 근거

ORD 기록
ord-1de94f9dd14241c49dc2f9fc7823b52f
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354895B1

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