Glycine → N-[(4-Bromophenyl)methyl]glycine

HRID 1891267Notes

Reaction equation

HRID 1891267 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[BH4-].[Na+]>C1COCC1.C(O)C.O>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:1][CH2:2][C:3]([OH:5])=[O:4])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 750GlycineHCID 14798Sodium HydroxideHCID 707414-BromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 28354373N-[(4-Bromophenyl)methyl]glycineYield 35.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To water (40 ml) was added glycine (246 mmol, 18.5 g) and aqueous sodium hydroxide (10M; 100 mmol, 10 ml). 4-Bromobenzaldehyde (130 mmol, 24 g) was added to afford a suspension. Ethanol (40 ml) and THF (90 ml) were added, followed by sodium borohydride (174 mmol, 6.6 g) and the mixture stirred at room temperature overnight. The reaction mixture was concentrated and washed with ether (×3) and the aqueous layer acidified to pH ˜6.5 at which point precipitation occurred. The solid was filtered and washed with water and diethyl ether before co-evaporation with toluene to give 2-(4-bromobenzylamino)acetic acid (7H2) 11.3 g; 1H NMR (400 MHz, DMSOd6) δ 7.56 (d, 2H) 7.38 (d, 2H) 3.85 (s, 2H) 3.10 (s, 2H).

Workup

  1. customto afford a suspension
  2. concentrationThe reaction mixture was concentrated
  3. washwashed with ether (×3)
  4. customthe aqueous layer acidified to pH ˜6.5 at which point precipitation
  5. filtrationThe solid was filtered
  6. washwashed with water and diethyl ether before co-evaporation with toluene

Sources & evidence

ORD record
ord-4628244d2bbd42ab84380213eeac6519
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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