Diisopropylethylamine → Tert-butyl[4-((2r,3s)-3-benzoylamino-2-hydroxy-3-phenylpropionylamino)benzyl]-carbamate

HRID 421294

Reaktionsgleichung

Reaktionsgleichung von HRID 421294
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[C:17]([NH:25][C@@H:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:27]([OH:31])[C:28](O)=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C=O)C>[C:10]([O:9][C:8](=[O:14])[NH:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([NH:1][C:28](=[O:29])[C@H:27]([OH:31])[C@@H:26]([NH:25][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:3][CH:4]=1)([CH3:12])([CH3:13])[CH3:11]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2733179PyBroPHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 2762289N-Benzoyl-3-phenylisoserine, (2R,3S)-

Produkt 1

HCID 24798298Tert-butyl[4-((2r,3s)-3-benzoylamino-2-hydroxy-3-phenylpropionylamino)benzyl]-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Analogously to Example 1, Process step 1, 33 mg (0.15 mmol) of tert-butyl (4-aminobenzyl)carbamate and 43 mg (0.15 mmol) of (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionic acid were dissolved in 1 ml of DCM and 1 ml of DMF and treated successively with 78 μl of DIPEA (0.45 mmol), 22.5 mg of HOAt (0.165 mmol) and 76.9 mg (0.165 mmol) of PyBrop. Without further work-up, the batch obtained was filtered and then purified using HPLC. The product-containing fractions were lyophilized.

Aufarbeitung

  1. customWithout further work-up, the batch obtained
  2. filtrationwas filtered
  3. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-cd6d0b9e14c84780b236df41a3438fee
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097758B2

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