Argatroban monohydrate → Methyl 6-aminohexanoate

HRID 1586271

Reaktionsgleichung

Reaktionsgleichung von HRID 1586271
C[C@H:2]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[N:5](C([C@@H](NS(C2C3NCC(C)CC=3C=CC=2)(=O)=O)CCCN=C(N)N)=O)[CH2:4][CH2:3]1.O.N[CH2:38]CCCCCCCCCCC(OC)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][C:8]([O:10][CH3:38])=[O:9]

Komponenten

5

Edukt 3

HCID 92721Argatroban monohydrateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 3665980Methyl 12-aminododecanoate

Produkt 1

HCID 1810164Methyl 6-aminohexanoateAusbeute 169,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of argatroban monohydrate (300 mg, 0.570 mmol) and methyl 12-aminododecanoate (compound YS-004-17) (132 mg, 0.576 mmol) in anhydrous DMF (15 mL) was added HBTU (258 mg, 0.680 mmol). Stirring was continued at room temperature for 16 hours. The precipitates formed during the reaction were filtered off and DMF was removed by vacuum distillation. The residue was purified by preparative TLC using solvents CH2Cl2 /MeOH/NH3 (90/10/1, v/v) to give the titled compound (140 mg) (Yield: 28%). 1HNMR (MeOH-4, 300 MHz).

Aufarbeitung

  1. customThe precipitates formed during the reaction
  2. filtrationwere filtered off
  3. customDMF was removed by vacuum distillation
  4. customThe residue was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-ded843c5ff40426aae07ba2e7782ea1a
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942620

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