Diisopropylethylamine → (S)-6-Hydroxy-2-{(S)-2-[(S)-3-(4-hydroxy-phenyl)-2-methyl-propionylamino]-4-methyl-pentanoylamino}-hexanoic acid methyl ester

HRID 58395ノート

反応式

HRID 58395 の反応式
C(OC(N[C@@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:13]([NH:15][C@@H:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([OH:19])=O)=[O:14])=O)C1C=CC=CC=1.[CH3:32][O:33][C:34](=[O:42])[C@@H:35]([NH2:41])[CH2:36][CH2:37][CH2:38][CH2:39][OH:40].[CH3:43]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:32][O:33][C:34](=[O:42])[C@@H:35]([NH:41][C:17](=[O:19])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([CH3:43])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)[CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:36][CH2:37][CH2:38][CH2:39][OH:40]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11680006AG-H-13503HCID 44191152Z-Tyr-Leu-OH

生成物 1

HCID 66847133(S)-6-Hydroxy-2-{(S)-2-[(S)-3-(4-hydroxy-phenyl)-2-methyl-propionylamino]-4-methyl-pentanoylamino}-hexanoic acid methyl ester収率 100.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl pentanoic acid (Bachem) (5.44 mmol, 1.36 g, 1 eq) and methyl ester 82 (5.44 mmol, 0.91 g) in DMF was added HATU (5.98 mmol, 1.41 g, 1.1 eq). DIPEA (0.12 mol, 1.62 g, 2.1 eq) was added and the reaction mixture was stirred at room temperature overnight. EtOAc (l 00 mL) was added the mixture was washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by recrystallisation from EtOAc to provide diol 83 as an oil (2.39 g, 76%).

後処理

  1. washwas washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by recrystallisation from EtOAc

出典と根拠

ORDレコード
ord-8b5b0905221345cf99c6fb1fa28a1657
出典データセット
uspto-grants-2016_09
特許番号
US09434762B2

反応ノート

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