(2S)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid → Boc-L-4-Bromophenylalaninol

HRID 1621213Notes

Reaction equation

HRID 1621213 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C@@H:7]([C:16](O)=[O:17])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C@H:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:16][OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2734477(2S)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 57594215Boc-L-4-BromophenylalaninolYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (72.6 mmol), in anhydrous diethyl ether (550 mL) at 0° C. was added slowly lithium aluminum hydride, 95% (108.9 mmol). The resulting solution was stirred for an additional 2 h at 0° C. The reaction was then carefully quenched with a saturated aqueous solution of sodium bicarbonate (73 mL) which stirred at RT for half an hour. Lithium aluminium salts crashed out of solution and were removed by filtration. The filtrate was concentrated and vacuum pumped for 24 h to afford the title product as a white solid (97%). ESMS [M+H]+: 331.2.

Workup

  1. customThe reaction was then carefully quenched with a saturated aqueous solution of sodium bicarbonate (73 mL) which
  2. stirringstirred at RT for half an hour
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated
  5. waitvacuum pumped for 24 h

Sources & evidence

ORD record
ord-cc68449dd4b04759a155dab287fd925b
Source dataset
uspto-grants-2014_07
Patent number
US08772507B2

Reaction notes

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