Phenyl isocyanate → 2-{3-[1-tert-Butoxycarbonyl-5-(4-trimethylstannanyl-benzylamino)-pentyl]-ureido}-pentanedioic acid di-tert-butyl ester

HRID 557468Notes

Reaction equation

HRID 557468 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:17][C:18]([NH:20][CH:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].C1(N=C=O)C=CC=CC=1.[CH3:44][Sn:45]([CH3:55])([CH3:54])[C:46]1[CH:53]=[CH:52][C:49]([CH:50]=O)=[CH:48][CH:47]=1>>[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:17][C:18]([NH:20][CH:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:50][C:49]1[CH:52]=[CH:53][C:46]([Sn:45]([CH3:44])([CH3:55])[CH3:54])=[CH:47][CH:48]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 7672Phenyl isocyanateHCID 138406964-Trimethylstannanyl-benzaldehydeHCID 744053812-[3-(5-Amino-1-tert-butoxycarbonyl-pentyl)-ureido]-pentanedioic acid di-tert-butyl ester

Product 1

HCID 668983092-{3-[1-tert-Butoxycarbonyl-5-(4-trimethylstannanyl-benzylamino)-pentyl]-ureido}-pentanedioic acid di-tert-butyl esterYield 40%

Procedure

The following compounds of the general structure 8 were prepared in overall yields ranging from 20-60% by the route depicted in Scheme B. The key synthetic intermediate (4) was reacted with the appropriate phenylisocyanate at room temperature to afford the desired protected intermediates (5) in good yields. The t-butyl ester protecting groups were removed in the presence of 50% TFA in DCM for 1 hour at room temperature. Upon completion, the reactions were concentrated on a rotary evaporator purified by HPLC or recrystallization to afford the desired products (6) in 40-90% yield.

Workup

  1. customThe following compounds of the general structure 8 were prepared
  2. customin overall yields
  3. customto afford the
  4. customThe t-butyl ester protecting groups were removed in the presence of 50% TFA in DCM for 1 hour at room temperature
  5. concentrationUpon completion, the reactions were concentrated on a rotary evaporator
  6. custompurified by HPLC or recrystallization

Sources & evidence

ORD record
ord-705202c735a64ff9a2cc789d13e54ddd
Source dataset
uspto-grants-2011_11
Patent number
US08058449B2

Reaction notes

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