Sodium borohydride → {3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic Acid Tert-butyl Ester

HRID 480320Notes

Reaction equation

HRID 480320 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[S:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:27][C:26]2[CH:25]=[CH:24][C:23]([C:19]3[S:18][CH:22]=[CH:21][N:20]=3)=[CH:30][CH:29]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeHCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Product 1

HCID 53752425{3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic Acid Tert-butyl EsterYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (3-aminomethyl-phenoxy)-acetic acid tert-butyl ester (0.14 g, 0.59 mmol) and 4-thiazol-2-yl-benzaldehyde (0.105 g, 0.55 mmol) in 2 mL MeOH was stirred at room temperature for 1.5 hours. After cooling to 0° C., NaBH4 (0.033 g, 0.88 mmol) was added and the reaction was stirred for 10 minutes. The mixture was quenched with aqueous saturated NaHCO3:H2O (1:1) and the MeOH was removed in vacuo. The product was extracted into CH2Cl2 and the organic solution was dried over MgSO4, filtered, and concentrated in vacuo to afford a brown oil. The product was purified via flash chromatography on silica gel (6/4 EtOAc/Hexanes) to afford the title compound of Step A (0.140 g). 1H NMR (400 MHz, CDCl3) δ 7.91 (d, 2H), 7.82 (s, 1H), 7.40 (d, 2H), 7.23-7.38 (m, 2H), 6.94 (m, 2H), 6.78 (d, 1H), 4.49 (s, 2H), 3.80 (s, 2H), 3.76 (s, 2H), 1.45 (s, 9H); MS 411 (M+1).

Workup

  1. customThe mixture was quenched with aqueous saturated NaHCO3:H2O (1:1)
  2. customthe MeOH was removed in vacuo
  3. extractionThe product was extracted into CH2Cl2
  4. dry with materialthe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a brown oil
  8. customThe product was purified via flash chromatography on silica gel (6/4 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-323b47008df440f0aea9c29293ae687a
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

Loading…