Methyl iodide → HCID 58109670, compound

HRID 2037564Notes

Reaction equation

HRID 2037564 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][C@@:12]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([OH:30])=[O:29])=[CH:23][CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[C:39]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][C@@:12]2([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][C:28]([O:30][CH3:39])=[O:29])=[CH:25][CH:26]=3)[CH3:20])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58109426HCID 58109426, compound

Product 1

HCID 58109670HCID 58109670, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(4-((S)-1-((R)-6-(3-(4-methoxybenzyloxy)propyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)acetic acid (260 mg, 0.50 mmol) and K2CO3 in DMF (2 mL) was added CH3I (0.2 g, 1 mmol). The resulting mixture was stirred overnight. The solid was filtered, and the filtrate was concentrated to give the crude product, which was purification by TLC to afford methyl 2-(4-((S)-1-((R)-6-(3-(4-methoxybenzyloxy)propyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)acetate (100 mg, 37%). 1H NMR (CDCl3): δ=1.42 (d, 3H), 1.68 (m, 1H), 1.88 (m, 2H), 2.12 (m, 1H), 2.23 (m, 2H), 2.78 (m, 1H), 3.29 (m, 2H), 3.44 (s, 2H), 3.64 (s, 3H), 3.75 (s, 3H), 4.28 (s, 2H), 5.56 (q, 1H), 6.73 (m, 4H), 6.92 (m, 2H), 7.14 (m, 2H), 7.25 (m, 5H).

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product, which
  4. custompurification by TLC

Sources & evidence

ORD record
ord-d77750d7982f46aa80f0b03e6cf58157
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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