Triethylamine → HCID 67408546, compound

HRID 1174202Notes

Reaction equation

HRID 1174202 reaction equation
Cl.[C:2]([O:6][C:7](=[O:14])[C@H:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[O:22]([CH2:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:11][C:10]([CH3:13])([CH3:12])[C@H:8]([NH:9][C:30](=[O:31])[CH2:29][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 56776989tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride

Product 1

HCID 67408546HCID 67408546, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of L-tert-Leucine tert-butyl ester hydrochloride (0.20 g, 0.90 mmol) in THF (9 mL) at 0° C. was treated with triethylamine (0.38 mL, 2.73 mmol) and phenoxyacetyl chloride (0.14 mL, 1.01 mmol), stirred at 0° C. for 15 minutes and then at 25° C. for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-10% ethyl acetate/chloroform to give the title compound (0.23 g, 80% yield).

Workup

  1. waitat 25° C. for 2 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 0-10% ethyl acetate/chloroform

Sources & evidence

ORD record
ord-d5b51487f8184198b58104bb85a48edf
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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