Acetic Acid → HCID 130473147, compound

HRID 2279953Notes

Reaction equation

HRID 2279953 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:31])[CH:5]=[C:6]([Cl:30])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH:28]=O)=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[NH2:32][CH:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:34]([O:36][CH:37]1[CH2:43][CH:42]2[N:44]([CH3:45])[CH:39]([CH2:40][CH2:41]2)[CH2:38]1)=[O:35].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:30][C:6]1[CH:5]=[N+:4]([O-:31])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][NH:32][CH:33]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:34]([O:36][CH:37]2[CH2:38][CH:39]3[N:44]([CH3:45])[CH:42]([CH2:41][CH2:40]3)[CH2:43]2)=[O:35])=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3049460HCID 3049460, compoundHCID 5049666Sodium triacetoxyborohydrideHCID 118142901HCID 118142901, compound

Product 1

HCID 130473147HCID 130473147, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]5-formylthiophene-2-carboxylate (0.17 g, 0.35 mmol), (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-amino-2-phenyl-acetate (0.14 g, 0.53 mmol) and acetic acid (40 μL, 0.71 mmol) in dichloromethane (8 mL) was stirred at room temperature for 20 h. Sodium triacetoxyborohydride was added and the reaction mixture was stirred at room temperature for a further 24 h. The mixture was diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (2×10 mL) and saturated sodium chloride solution (10 mL). The organic layer was separated and filtered through a phase separator and the solvent was removed by evaporation under reduced pressure. Purification by preparative HPLC gave the title compound (mixture of diastereoisomers) as a pale yellow solid (72 mg, 28%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 24 h
  2. washwashed with saturated sodium bicarbonate solution (2×10 mL) and saturated sodium chloride solution (10 mL)
  3. customThe organic layer was separated
  4. filtrationfiltered through a phase separator
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2f2030e8128740529d62ac5350383d13
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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