Pyridine → HCID 122638429, compound

HRID 1482391Notes

Reaction equation

HRID 1482391 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:25])[C@@H:19]([CH2:23][OH:24])[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:26][O:27][C:28]1[CH:49]=[CH:48][C:31]([C:32](Cl)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1.[N:50]1[CH:55]=[CH:54]C=[CH:52][CH:51]=1>>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:25])[C@@H:19]([CH2:23][O:24][C:32]([C:31]3[CH:48]=[CH:49][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:20]([O-:22])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1.[CH2:55]([NH+:50]([CH:49]([CH3:48])[CH3:28])[CH:51]([CH3:52])[CH3:1])[CH3:54]

Participants

4

Reactant 3

HCID 1049PyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 11416557HCID 11416557, compound

Product 1

HCID 122638429HCID 122638429, compoundYield 92%

Procedure

(2S)-2-[9H-Fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-hydroxypropanoic acid (Compound SP823) (920 mg, 2.70 mmol) was dissolved in dehydrated pyridine (2.5 mL), and the reaction solution was concentrated under reduced pressure. This operation was repeated twice, after which the reaction solution was dissolved in dehydrated pyridine (2.5 mL) under a nitrogen atmosphere, and 4,4′-dimethoxytrityl chloride (931 mg, 2.75 mmol) was added at room temperature. The reaction mixture was stirred at the same temperature for 13 hours and then concentrated under reduced pressure. The resulting residue was dissolved in chloroform (15 mL) and washed with saturated sodium bicarbonate (5 mL). The organic layer was dried over sodium sulfate and then concentrated under reduced pressure, and the resulting crude product was purified by normal-phase silica gel column chromatography (1% diisopropylethylamine-containing dichloromethane/methanol) to afford N-ethyl-N-isopropylpropan-2-aminium (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(bis(4-methoxyphenyl)(phenyl)methoxy)propanoate (Compound SP816) (1.92 g, 92%).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. dissolutionafter which the reaction solution was dissolved in dehydrated pyridine (2.5 mL) under a nitrogen atmosphere
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in chloroform (15 mL)
  5. washwashed with saturated sodium bicarbonate (5 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting crude product was purified by normal-phase silica gel column chromatography (1% diisopropylethylamine-containing dichloromethane/methanol)

Sources & evidence

ORD record
ord-a57e7b2d4c394075be672f43c558708b
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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