Carbon tetrabromide → Boc-L-alanine methyl ester

HRID 1972182Notes

Reaction equation

HRID 1972182 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13]O)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[C:9]([O:8][C:6]([NH:5][C@@H:4]([CH3:13])[C:3]([O:2][CH3:1])=[O:15])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 10856577Boc-L-alanine methyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The obtained N-Boc-L-serine methyl ester (6.0 g) and 10.5 g (1.2 eq) of carbon tetrabromide were dissolved in 100 ml of dry THF and a solution prepared by dissolving 8.29 g (1.2 eq) of Ph3P in 50 ml of dry THF was added dropwise under ice cooling, followed by stirring at room temperature for 24 hours. After the reaction, the reaction solution was filtered and purified by silica gel column chromatography to obtain 4.9 g (65%) of methyl(S)-2-tert-butoxycarbonylaminopropanate as a white crystal.

Workup

  1. customa solution prepared
  2. additionwas added dropwise under ice cooling
  3. customAfter the reaction
  4. filtrationthe reaction solution was filtered
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a63ea6edc7c44adb2b396e0be0f29a5
Source dataset
uspto-grants-2013_04
Patent number
US08431738B2

Reaction notes

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