Methanol → HCID 78010199, compound

HRID 927841Notes

Reaction equation

HRID 927841 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.[NH2:18][CH:19]([CH:23]1[CH2:25][CH2:24]1)[C:20]([NH2:22])=[O:21].CO>CCCCCCC>[C:20]([CH:19]([NH:18][C:15]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[N:8]=1)=[O:17])[CH:23]1[CH2:25][CH2:24]1)(=[O:21])[NH2:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 61310151HCID 61310151, compoundHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 78010199HCID 78010199, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42a) and α-amino-cyclopropaneacetamide (CAN 1100749-41-4) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/20% 2-propanol as eluent. The (+)-enantiomer was isolated. LC-MS (UV peak area/ESI) 97.7%, 330.1804 (M+H)+, αD20 (MeOH)=+43.3°.

Workup

  1. customThe product was isolated by chiral chromatography on Chiralpak AD
  2. customThe (+)-enantiomer was isolated

Sources & evidence

ORD record
ord-af135896997e4b7c8d4ca8773f666cef
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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