Cesium bicarbonate → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

HRID 1441190Notes

Reaction equation

HRID 1441190 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+]([O-])=O)=[CH:6][CH:5]=1.C(=O)(O)[O-].[Cs+]>CO>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 2734983Cesium bicarbonateHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Boc-Phe(4-NO2)-OH (1.39 g) was dissolved in 70% methanol (100 ml) and adjusted to pH7 with the addition of 1N caesium bicarbonate. The solution was evaporated to dryness with the residue being evaporated three more times with added DMF. The resultant dried caesium salt of Boc-Phe(NO2)-OH was dissolved in DMF (60 ml) and shaken with BrCH2 -Pam-resin (1 meq of Br) overnight. Boc-Phe(4-NO2 --OCH2 -Pam-resin was isolated by filtration, washed with DCM and treated according to Table 1 (steps 10-14) to give the title compound as a free base.

Workup

  1. customThe solution was evaporated to dryness with the residue
  2. custombeing evaporated three more times with added DMF
  3. dissolutionThe resultant dried caesium salt of Boc-Phe(NO2)-OH was dissolved in DMF (60 ml)

Sources & evidence

ORD record
ord-5f3ba832a46f4399a82740d0dc47e25d
Source dataset
uspto-grants-1996_03
Patent number
US05502164

Reaction notes

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