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Acetic Acid → 2-(4-((((R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl) phenoxy)methyl)benzoate

HRID 2205693
Notes
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Reaction equation

HRID 2205693 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([C:6]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10](=[O:17])[NH:11]2)[OH:5].C(N(CC)CC)C.[C:25]1([C@H:31]([NH:61][C:62]([O:64][C@@H:65]2[CH:70]3[CH2:71][CH2:72][N:67]([CH2:68][CH2:69]3)[CH2:66]2)=[O:63])[C:32]2[CH:33]=[C:34]([CH:58]=[CH:59][CH:60]=2)[O:35][CH2:36][C:37]2[CH:57]=[CH:56][C:40]([C:41]([O:43][CH2:44][CH2:45][O:46][C:47]3[CH:52]=[CH:51][C:50]([CH:53]=O)=[CH:49][C:48]=3[CH3:55])=[O:42])=[CH:39][CH:38]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CO>[C:25]1([C@H:31]([NH:61][C:62]([O:64][C@@H:65]2[CH:70]3[CH2:71][CH2:72][N:67]([CH2:68][CH2:69]3)[CH2:66]2)=[O:63])[C:32]2[CH:33]=[C:34]([CH:58]=[CH:59][CH:60]=2)[O:35][CH2:36][C:37]2[CH:57]=[CH:56][C:40]([C:41]([O:43][CH2:44][CH2:45][O:46][C:47]3[CH:52]=[CH:51][C:50]([CH2:53][NH:2][CH2:3][C@H:4]([OH:5])[C:6]4[CH:15]=[CH:14][C:13]([OH:16])=[C:12]5[C:7]=4[CH:8]=[CH:9][C:10](=[O:17])[NH:11]5)=[CH:49][C:48]=3[CH3:55])=[O:42])=[CH:39][CH:38]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 71093241(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochlorideHCID 867208162-(4-formyl-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate

Product 1

HCID 74763946
2-(4-((((R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl) phenoxy)methyl)benzoate
Yield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of (R)-5-(2-amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochloride (0.211 g, 0.83 mmol) in methanol (6 mL) was added triethylamine (0.229 mL, 1.65 mmol). The mixture was stirred for 10 minutes and then a solution of 2-(4-formyl-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate (0.445 g, 0.69 mmol) in methanol (2 mL) was added. The mixture was stirred at RT for 1 hour. Sodium triacetoxyborohydride (0.292 g, 1.38 mmol) followed by acetic acid (0.188 mL, 3.28 mmol) added and the reaction continued for a further 18 hours. The reaction mixture was quenched with water and evaporated at reduced pressure. The residue dissolved in iso-butanol and washed with water. The organic phase was evaporated at reduced pressure and the crude material was purified by reverse phase preparative HPLC to afford the title compound (0.065 g, 11%)

Workup

  1. stirringThe mixture was stirred at RT for 1 hour
  2. additionadded
  3. waitthe reaction continued for a further 18 hours
  4. customThe reaction mixture was quenched with water
  5. customevaporated at reduced pressure
  6. dissolutionThe residue dissolved in iso-butanol
  7. washwashed with water
  8. customThe organic phase was evaporated at reduced pressure
  9. customthe crude material was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-9b8c98cb28a946e0bf1abc090eba4c73
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371318B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes