Trimethylamine → HCID 86641208, compound

HRID 1958698Notes

Reaction equation

HRID 1958698 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][O:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:27]([CH3:30])([CH3:29])[CH3:28]>CCO>[CH3:26][S:23]([O-:25])(=[O:24])=[O:22].[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:21][N+:27]([CH3:30])([CH3:29])[CH3:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 129270567HCID 129270567, compound

Product 1

HCID 86641208HCID 86641208, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of (R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)-butanoate (149 mg, 0.38 mmol) in EtOH (2 mL) at 0° C. was added xs Me3N in EtOH (4.2 M, 2 mL, 8.4 mmol). The reaction was sealed and stirred at the temperature for 15 min and then at rt for 3 d. Later, the reaction was concentrated to dryness and purified by preparative TLC (silica gel, 5% MeOH/DCM) to afford the title compound as a colorless gum (43 mg, 37%). 1H NMR (300 MHz, CDCl3): δ=7.35-7.20 (m, 5H), 5.14-5.00 (AB quartet, J=12 Hz, 2H), 4.46 (br, 1H), 3.50-3.25 (m, 2H), 3.24 (s, 9H), 2.85-2.65 (m 2H), 2.70 (s, 3H), 1.38 (s, 9H); MS ESI [M]+, calcd for [C19H31N2O4]+ 351.5 found 351.2 m/z (100).

Workup

  1. customThe reaction was sealed
  2. waitat rt for 3 d
  3. concentrationLater, the reaction was concentrated to dryness
  4. custompurified by preparative TLC (silica gel, 5% MeOH/DCM)

Sources & evidence

ORD record
ord-0e2dd57408e8438eb6ad06407753901b
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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