Hydrochloric Acid → 1522241-50-4

HRID 595247Notes

Reaction equation

HRID 595247 reaction equation
[ClH:1].[N+](=[CH:4][C:5](=[O:16])[C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7])=[N-]>C(OCC)C>[Cl:1][CH2:4][C:5](=[O:16])[C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 101153814HCID 101153814, compound

Product 1

HCID 964820041522241-50-4

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrochloric acid (2.0 M in water, 21.4 mL, 42.8 mmol) was added to a mixture of (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate (1.89 g, 8.86 mmol) in diethyl ether (19.27 mL) at 0° C.0. The mixture was stirred vigorously for 20 minutes and then allowed to warm to room temperature and stirred vigorously until the mixture went from yellow to colorless. The mixture was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.34 (d, J=7.0 Hz, 1H), 4.64-4.51 (m, 2H), 4.23-4.02 (m, 1H), 1.36 (s, 9H), 1.16 (d, J=7.2 Hz, 3H).

Workup

  1. stirringstirred vigorously until the mixture
  2. washThe mixture was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-095cc7a019cb459299529b14ab7378e7
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

Loading…