Dimethylamine → HCID 59294375, compound

HRID 1958699Notes

Reaction equation

HRID 1958699 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21]OS(C)(=O)=O)[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].[NH:27]([CH3:29])[CH3:28]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][N:27]([CH3:29])[CH3:28])[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]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 129270567HCID 129270567, compound

Product 1

HCID 59294375HCID 59294375, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a sealed vial, (R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)-butanoate (130.8 mg, 0.34 mmol) was stirred at rt in a THF solution of Me2NH (2.0 M, 10 mL, 20 mmol) for 3 d. Then the reaction was concentrated under reduced pressure and purified by preparative TLC (0.5% MeOH in DCM, and then 5% MeOH/DCM) to afford the title compound as a colorless gum (28 mg, 25%). 1H NMR (300 MHz, CDCl3): δ=7.85-7.25 (m, 5H), 5.25-5.00 (m, 2H), 4.15 (br s, 1H), 2.58-2.50 (m, 4H), 2.41 (br s, 6H), 1.39 (s, 9H); MS ESI [M]+, calcd for [C18H28N2O4+H]+ 336.4 found m/z 337.2 (100).

Workup

  1. concentrationThen the reaction was concentrated under reduced pressure
  2. custompurified by preparative TLC (0.5% MeOH in DCM

Sources & evidence

ORD record
ord-c300d8c154c5418e8102931d3f0faabf
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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