4-Chlorobenzoyl chloride → HCID 67772465, compound

HRID 1808797Notes

Reaction equation

HRID 1808797 reaction equation
[CH3:1][CH:2]([CH3:8])[C@H:3]([NH:6][CH3:7])[CH2:4][OH:5].[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[C:19]([O-:22])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:5][CH2:4][C@@H:3]([N:6]([CH3:7])[C:19](=[O:22])[C:13]2[CH:17]=[CH:18][C:10]([Cl:9])=[CH:11][CH:12]=2)[CH:2]([CH3:8])[CH3:1])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 10340Sodium CarbonateHCID 12695788(2S)-3-Methyl-2-(methylamino)butan-1-ol

Product 1

HCID 67772465HCID 67772465, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TEA (4.73 mL, 34.1 mmol) was added to (S)-3-methyl-2-(methylamino)butan-1-ol (Compound B2.1) (1 g, 8.5 mmol) in DCM (10 mL). The mixture was cooled on an ice-bath and 4-chlorobenzoyl chloride (3.14 g, 17.9 mmol) in DCM (10 mL) was dropwise (over 10 min) added. The resultant mixture was stirred at rt for 2 h. The organic phase was washed with Na2CO3 (8 wt %, 40 mol) and concentrated under reduced pressure to give the title compound (3.3 g, 98%). The obtained crude product was used without further purification. LCMS (M+H)+: 394. Mixture of rotamers: 1H NMR (600 MHz, CD3OD) δ 0.93-1.04 (m), 1.13 (d), 1.98-2.13 (m), 2.87 (s), 3.02 (s), 3.60-3.74 (m), 4.43-4.73 (m), 7.16-7.64 (m), 7.87-8.19 (m). Total number of protons: 21.

Workup

  1. temperatureThe mixture was cooled on an ice-bath
  2. custom(over 10 min)
  3. additionadded
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb0ef309b8654a62b17e8474ace0b8d1
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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