Hydrochloric Acid → ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate

HRID 222449Notes

Reaction equation

HRID 222449 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][OH:9])[CH3:2].C(N(CC)CC)C.CS(C)=O.Cl>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]=[O:9])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 57351319Ethyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate

Product 1

HCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoateYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Under atmosphere of argon, to a solution of (4R)-5-hydroxy-4-t-butoxycarbonylaminopentanoic acid ethyl ester (15.0 g), triethylamine (32.0 mL) and dimethylsulfoxide (39 mL) in ethyl acetate (120 mL), a solution of sulfur trioxide pyridine complex (18.3 g) in mixed solvent ethyl acetate (30 mL) and dimethylsulfoxide (75 mL) was added at 0° C., and the mixture was stirred for 1 hour. The reaction mixture was added by water (5 mL) at 0° C. and was added by 1N hydrochloric acid (240 mL). Separated aqueous layer was extracted by ethyl acetate. The combined organic layer was washed with water and brine successively, dried over an anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (14.7 g) having the following physical data.

Workup

  1. extractionSeparated aqueous layer was extracted by ethyl acetate
  2. washThe combined organic layer was washed with water and brine successively
  3. dry with materialdried over an anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-052e1632a2c44812bd295e9f2c245524
Source dataset
uspto-grants-2012_06
Patent number
US08207223B2

Reaction notes

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