Water → HCID 90281918, compound

HRID 1497542Notes

Reaction equation

HRID 1497542 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[S:6][CH:7]=1.Cl.[NH2:16][C@H:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:18].C(N(CC)CC)C.O>CN(C)C=O>[C:22]([O:21][C:19](=[O:20])[C@@H:17]([NH:16][CH2:2][C:3]1[CH:4]=[C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[S:6][CH:7]=1)[CH3:18])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11275390tert-Butyl alaninate hydrochlorideHCID 59478359HCID 59478359, compound

Product 1

HCID 90281918HCID 90281918, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(bromomethyl)thiophene-2-carboxylate (2.00 g) in N,N-dimethylformamide (19.8 mL) were added tert-butyl L-alaninate hydrochloride (2.62 g) and triethylamine (4.02 mL), followed by heating at 60° C. for 12 hours. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-({[(2S)-1-tert-butoxy-1-oxopropan-2-yl]amino}methyl)thiophene-2-carboxylate (1.31 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bfd37d0e48d94fe5b97505a41a3cab28
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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