Sodium triacetoxyborohydride → HCID 178483935, compound

HRID 630395Notes

Reaction equation

HRID 630395 reaction equation
[OH:1][C:2]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)([C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22](C=O)=[CH:21][C:20]=2[Cl:27])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4].C([O-])(=O)C.C([Si](C)(C)O[C@H](C1C=CC(O)=C2C=1C=CC(=O)N2)C[NH3+])(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:79]([Si:83]([CH3:135])([CH3:134])[O:84][C@H:85]([C:122]1[CH:131]=[CH:130][C:129]([OH:132])=[C:128]2[C:123]=1[CH:124]=[CH:125][C:126](=[O:133])[NH:127]2)[CH2:86][NH:87][CH2:88]C1C=CC(OCCCN(C)[C@H]2CC[C@H](OC(C3SC=CC=3)(C3SC=CC=3)C([O-])=O)CC2)=CC=1)([CH3:82])([CH3:81])[CH3:80]>>[OH:1][C:2]([C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:88][NH:87][CH2:86][C@H:85]([O:84][Si:83]([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:135])[CH3:134])[C:122]3[CH:131]=[CH:130][C:129]([OH:132])=[C:128]4[C:123]=3[CH:124]=[CH:125][C:126](=[O:133])[NH:127]4)=[CH:21][C:20]=2[Cl:27])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 4

HCID 5049666Sodium triacetoxyborohydrideHCID 67145275[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-(8-hydroxy-2-oxo-1H-quinolin-5-yl)ethyl]azanium acetateHCID 178483882HCID 178483882, compoundHCID 178483937HCID 178483937, compound2×

Product 1

HCID 178483935HCID 178483935, compound

Procedure

Obtained as a white solid (65%) starting from trans-4-((3-(2-chloro-4-formylphenylamino)-3-oxopropyl)(methyl)amino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 50; 54 mg, 0.10 mmol), (2R)-2-{[tert-butyl(dimethyl)-silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethanaminium acetate (prepared according to preparation 8 from US20060035931) (57 mg, 0.14 mmol) and sodium triacetoxyborohydride (77 mg, 0.35 mmol) following the experimental procedure as described in intermediate 30 followed by a purification by preparative reversed-phase HPLC (CHCl3 to CHCl3/MeOH 95:5).

Workup

  1. customfollowed by a purification by preparative reversed-phase HPLC (CHCl3 to CHCl3/MeOH 95:5)

Sources & evidence

ORD record
ord-4ae01ae5cdc442ed91cc58837aeb7748
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…