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Water → 4(Aminomethyl)-2-phenylbenzoyl methionine methyl ester

HRID 2121245
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HRID 2121245 반응식
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]=[N+]=[N-])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH3:5].[C:3]([O:2][CH2:1][CH3:29])(=[O:28])[CH3:4].[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

6

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 20622822[4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

생성물 2

HCID 18464838Ammonia ethyl acetate수율 1%HCID 206228204(Aminomethyl)-2-phenylbenzoyl methionine methyl ester수율 193.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of the product of Example 332B (1.00 g, 2.5 mmol) and triphenylphosphine (0.98 g, 3.75 mmol) in THF (10 mL) was heated at reflux for 4 hours. The reaction mixture was cooled to ambient temperature, water (0.45 mL) was added, and the reaction mixture was stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (25% ethyl acetate-hexane, then 1% ammonia-ethyl acetate) gave the desired compound as a colorless oil (900 mg, 97%).

후처리

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-80f5081cefb64f189b8422d3db18724d
출처 데이터셋
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06693123B2

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