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

HRID 2371338노트

반응식

HRID 2371338 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionyl-amino]-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 (100 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9df7d80dd18c411488fbc97ce5a32c09
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710178B2

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