Imidazole → N-(benzyloxycarbonyl)-3(S)-iodomethy-beta-alanine tert-butyl ester

HRID 843722Notes

Reaction equation

HRID 843722 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][C@@H:8]([CH2:20]O)[NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:47]I>>[C:1]([O:5][C:6](=[O:22])[CH2:7][C@@H:8]([CH2:20][I:47])[NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 15043090(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 10971821N-(benzyloxycarbonyl)-3(S)-iodomethy-beta-alanine tert-butyl ester

Procedure

A mixture of N-benzyloxycarbonyl-3(S)-hydroxymethyl -β-alanine tert-butyl ester (2.0 g), triphenylphosphine (1.87 g), imidazole (0.66 g) and I2 (1-80 g) was stirred for 30 minutes at room temperature. The precipitate was filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5% (EtOAc/n-hexane) to give N-benzyloxycarbonyl-3(S)-iodomethyl-β-alanine tert-butyl ester (1.8 g) as a white solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with 5% (EtOAc/n-hexane)

Sources & evidence

ORD record
ord-698b1248d8a847289b9b1e92f664dbfc
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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