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Hydrochloric Acid → 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide

HRID 1818652
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HRID 1818652 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][NH:15][CH:16]=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[CH:12].C(N(CC)CC)C.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[C:37]1([CH2:43][CH2:44][CH:45]=[O:46])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:46][CH:45]([CH2:44][CH2:43][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:16]([NH:15][CH2:14][CH2:13][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]#[CH:12])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 8471TriethylamineHCID 94429TriphosgeneHCID 11379286Formamide, N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-

생성물 1

HCID 578850672-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide

시약·촉매·용매

2
HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매4회

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온도
-78 °C

실험 절차

N-[2-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide (8.0 g, 34 mmol) and triethylamine (8.3 g, 82 mmol) are dissolved in dichloromethane (80 ml). Bis(trichloromethyl) carbonate (triphosgene, 4.0 g, 14 mmol) in dichloromethane (40 ml) is added at +5° C. The mixture is stirred for 4 hours at +5° C. and then cooled to −78° C. A solution of titanium tetrachloride (7.0 g, 38 mmol) in dichloromethane (70 ml) is added and the mixture is stirred for 2 hours at −40° C. 3-Phenylpropionaldehyde (4.8 g, 36 mmol) in dichloromethane (50 ml) is added dropwise and the mixture is stirred for 17 hours at room temperature. The mixture is hydrolysed with 5N HCl (25 ml), stirred 30 minutes at room temperature and washed with water. After evaporation of the organic layer the residue is submitted to flash-chromatography (ethyl acetate/hexane 6:3) to give 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide (Compound E1.01).

후처리

  1. stirringthe mixture is stirred for 2 hours at −40° C
  2. stirringthe mixture is stirred for 17 hours at room temperature
  3. stirringstirred 30 minutes at room temperature
  4. washwashed with water
  5. customAfter evaporation of the organic layer the residue

출처 및 근거

ORD 기록
ord-63e648549493420c9fbcc536df3700c5
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07601674B2

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