Diisopropylethylamine → (R)-2-Amino-N-hydroxy-3-phenyl-propionamide

HRID 722442

반응식

HRID 722442 반응식
C1C2C(COC([NH:18][C@@H:19]([C:27]([OH:29])=O)[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.[B-](F)(F)(F)F.CN(C([O:42][N:43]1C(=O)C=CC=C1)=[N+](C)C)C.C(N(C(C)C)C(C)C)C.ClCCl.N1CCCCC1>ClCCl.CC(N(C)C)=O>[NH2:18][C@H:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]([NH:43][OH:42])=[O:29]

참가 물질

6

반응물 4

HCID 81531Diisopropylethylamine2회HCID 978332(2R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid2회HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate2회HCID 67144590Dichloromethane piperidine

생성물 1

HCID 10899270(R)-2-Amino-N-hydroxy-3-phenyl-propionamide

시약·촉매·용매 1

HCID 85741463dichloromethane N,N-dimethylacetamide용매2회

실험 절차

To a solution of N-(9-fluorenylmethoxycarbonyl)-D-phenylalanine (2.09 g, 5.4 mmol) in dry dichloromethane/DMA 1:1 (20 ml) are added TPTU (1.76 g, 5.94 mmol) and N-ethyldiiso-propylamine (1.02 ml, 5.94 mmol). After stirring for 5 min the mixture is added to aminooxy-2-chlorotrityl polystyrene resin (2.8 g, 2.7 mmol; Tetrahedron Lett. 1997, 38, 3311–3314) and the resulting suspension shaken at r.t. for 16 h. The mixture is filtered and the resin washed alternating with DMA and dichloromethane (3×). The described coupling procedure is repeated with a freshly prepared mixture of N-(9-fluorenylmethoxycarbonyl)-D-phenylalanine (2.09 g, 5.4 mmol), TPTU (1.76 g, 5.94 mmol) and N-ethyldiisopropylamine (1.02 ml, 5.94 mmol) in dichloromethane/DMA 1:1 (20 ml). After 16 h the suspension is filtered and the resin washed with DMA (2×), alternating with H2O and DMA (2×), alternating with 2-propanol and THF (3×), THF (2×) and dichloromethane (3×). The resin thus obtained is shaken for 30 min with a freshly prepared solution of dichloromethane/piperidine 8:2 (25 ml). After filtration, this process is repeated twice with fresh dichloromethane/piperidine solutions. The suspension is filtered, the resin washed with dichloromethane (2×), alternating with 2-propanol and dichloromethane (2×), dichloromethane (3×) and dried in vacuo, thus providing polymer-bound (R)-2-amino-N-hydroxy-3-phenyl-propionamide.

후처리

  1. stirringthe resulting suspension shaken at r.t. for 16 h
  2. filtrationThe mixture is filtered
  3. washthe resin washed
  4. filtrationAfter 16 h the suspension is filtered
  5. washthe resin washed with DMA (2×)
  6. customThe resin thus obtained
  7. filtrationAfter filtration
  8. filtrationThe suspension is filtered
  9. washthe resin washed with dichloromethane (2×)
  10. dry with materialdried in vacuo, thus providing polymer-bound (R)-2-amino-N-hydroxy-3-phenyl-propionamide

출처 및 근거

ORD 기록
ord-d2f7dda542a244319dd3c449b8eb1e57
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138432B1

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