Diisopropylethylamine → HCID 57945067, compound

HRID 1365016Notes

Reaction equation

HRID 1365016 reaction equation
[NH2:1][C@@H:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)C(C)C)(C)C.[F:20][C:21]([F:36])([F:35])[C:22]([O:25][C:26](=O)[O:27]C1C=CC=CN=1)([CH3:24])[CH3:23]>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C@@H:2]([NH:1][C:26]([O:25][C:22]([CH3:24])([CH3:23])[C:21]([F:36])([F:35])[F:20])=[O:27])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11309583Methyl L-tert-leucinateHCID 23595245Pyridin-2-yl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate

Product 1

HCID 57945067HCID 57945067, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (S)-methyl 2-amino-3,3-dimethylbutanoate (0.411 g, 2.262 mmol) in DCM (20 mL) was added N,N-Diisopropylethylamine (1.182 mL, 6.79 mmol). The formed solution was stirred for 5 min before addition of carbonic acid pyridin-2-yl ester 2,2,2-trifluoro-1,1-dimethyl-ethyl ester (1.24 g, 4.98 mmol, from step 1a) in DCM (10 mL). The final light yellow solution was stirred at room temperature overnight. The reaction mixture was washed with 5% citric acid aqueous solution, 0.1 M NaOH aqueous solution, and brine, then dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by silica gel column, eluted with (4:1) hexane-EtOAc to afford a colorless oil as the product (673 mg, 99%).

Workup

  1. washThe reaction mixture was washed with 5% citric acid aqueous solution, 0.1 M NaOH aqueous solution, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel column
  6. washeluted with (4:1) hexane-EtOAc

Sources & evidence

ORD record
ord-ac93bf84522f47d9b091fbb6b4eb27d4
Source dataset
uspto-grants-2011_02
Patent number
US07888464B2

Reaction notes

Loading…