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Triethylamine → HCID 59608133、化合物

HRID 1469687
ノート
印刷プレビュー

反応式

HRID 1469687 の反応式
[CH3:1][O:2][C:3]1[O:4][C:5]([C:8]([OH:10])=O)=[CH:6][N:7]=1.Cl.[NH2:12][C@H:13]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)[CH2:14][C@@H:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([CH2:22][C@@H:13]([NH:12][C:8]([C:5]2[O:4][C:3]([O:2][CH3:1])=[N:7][CH:6]=2)=[O:10])[CH2:14][C@@H:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:28][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25017086(2R,4S)-4-amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochlorideHCID 553038672-Methoxyoxazole-5-carboxylic acid

生成物 1

HCID 59608133HCID 59608133、化合物

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-methoxyoxazole-5-carboxylic acid, intermediate 22, (68 mg, 0.47 mmol) in DMF (2 mL) and DCM (2 mL) is added (2R,4S)-ethyl 4-amino-5-(biphenyl-4-yl)-2-methylpentanoate hydrochloride (150 mg, 0.43 mmol), HATU (246 mg, 0.65 mmol), and triethylamine (180 μL, 1.29 mmol). After stirring the reaction for 2 hours at room temperature, the reaction is quenched with H2O, and the crude is diluted in EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN), and then lyophilized to give (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-methoxyoxazole-5-carboxamido)-2-methylpentanoate (175 mg). HPLC retention time=1.71 minutes (condition A); MS 437.5 (M+1); 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.20 (d, J=7.1 Hz, 3 H) 1.25 (t, J=7.1 Hz, 3 H) 1.65 (ddd, J=14.3, 10.0, 4.3 Hz, 1 H) 1.96-2.10 (m, 1 H) 2.63 (ddd, J=9.4, 7.1, 4.2 Hz, 1 H) 2.92 (dd, J=13.9, 6.3 Hz, 1 H) 2.99 (dd, J=13.9, 6.3 Hz, 1 H) 4.11 (s, 3 H) 4.12-4.18 (m, 2 H) 4.34-4.54 (m, 1 H) 6.15 (d, J=8.8 Hz, 1 H) 7.28 (d, J=8.3 Hz, 2 H) 7.31-7.37 (m, 1 H) 7.40-7.47 (m, 3 H) 7.54 (d, J=8.3 Hz, 2 H) 7.59 (dd, J=8.3, 1.26 Hz, 2 H)

後処理

  1. customthe reaction for 2 hours at room temperature
  2. customthe reaction is quenched with H2O
  3. additionthe crude is diluted in EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue is purified by RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN)

出典と根拠

ORDレコード
ord-226e28057a5a49bd90a856fed0ae538d
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006249B2

反応ノート

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