Acetic Acid Mixture with Hydrobromic Acid → HCID 53747170, compound

HRID 1634026Notes

Reaction equation

HRID 1634026 reaction equation
[N+](=[CH:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N-].[BrH:23].C(O)(=O)C>CCOCC>[Br:23][CH2:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86587969HCID 86587969, compound

Product 1

HCID 53747170HCID 53747170, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution comprised of tert-butyl(S)-3-diazo-2-oxo-1-phenethylpropylcarbamate (7.09 g, 23.4 mmol) in ether (100 mL) was cooled to −10° C. and a solution comprised of hydrogen bromide/acetic acid (4.66 mL, 30% by weight) in ether (30 mL) was added dropwise. The mixture was stirred for 30 minutes and then ether (200 mL) was added. The mixture was washed with brine (50 mL), saturated aqueous sodium bicarbonate (150 mL), brine (50 mL), dried (MgSO4), filtered, and concentrated. Product was crystallized from hexane, to provide tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate (5.29 g, 14.7 mmol). 1H NMR (CDCl3): δ 1.44 (9H, s, t-Bu), δ 1.86 (1H, m, one CH2CH2C6H5), δ 2.18 (1H, m, other CH2CH2C6H5), δ 2.67 (2H, t, J=7.7 Hz, CH2CH2C6H5), δ 3.99 (2H, 2×d, J=13 Hz, CH2Br), δ 4.53 (1H, m, CHNH), δ 5.08 (1H, br.D, 5 Hz, NH), δ 7.17-7.29 (5H, m, aromatic H).

Workup

  1. additionwas added dropwise
  2. washThe mixture was washed with brine (50 mL), saturated aqueous sodium bicarbonate (150 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customProduct was crystallized from hexane

Sources & evidence

ORD record
ord-dc1fa783152e4393969db004564fda5e
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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