Acetic Acid → 3-(2-{6-methyl-2-oxo-3-[(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-ylmethyl)-amino]-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

HRID 322539Notes

Reaction equation

HRID 322539 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@H:6]([NH:13][C:14](=[O:25])[CH2:15][N:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH2:23])[C:17]1=[O:24])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[N:27]1[C:36]2[NH:35][CH2:34][CH2:33][CH2:32][C:31]=2[CH:30]=[CH:29][C:28]=1[CH:37]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@H:6]([NH:13][C:14](=[O:25])[CH2:15][N:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH:23][CH2:37][C:28]2[CH:29]=[CH:30][C:31]3[CH2:32][CH2:33][CH2:34][NH:35][C:36]=3[N:27]=2)[C:17]1=[O:24])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehydeHCID 540690173-(2-{6-methyl-2-oxo-3-amino-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

Product 1

HCID 543298343-(2-{6-methyl-2-oxo-3-[(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-ylmethyl)-amino]-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of the amine 16-6 (155 mg, 0.433 mmol), the aldehyde 14-3 (70 mg, 0.433 mmol) in CH2ClCH2Cl was added crushed 4 Å seives, AcOH (20 μL) and then NaB(OAc)3H (184 mg, 0.866 mmol). After stirring for 48 hours, the mixture was filtered through celite, poured into EtOAc and washed with saturated NaHCO3 then brine. The dried (MgSO4) solution was concentrated in vacuo to give a foam type solid. Column chromatography (5% MeOH in CHCl3) afforded the title compound 16-7 as a foam type solid.

Workup

  1. filtrationthe mixture was filtered through celite
  2. additionpoured into EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialThe dried (MgSO4) solution
  5. concentrationwas concentrated in vacuo
  6. customto give a foam type solid

Sources & evidence

ORD record
ord-824a727d736c437d85c154ff52a73fa8
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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