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

HRID 2121245
ノート
印刷プレビュー

反応式

HRID 2121245 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 2

HCID 18464838Ammonia ethyl acetate収率 1%HCID 206228204(Aminomethyl)-2-phenylbenzoyl methionine methyl ester収率 193.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-80f5081cefb64f189b8422d3db18724d
出典データセット
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06693123B2

反応ノート

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