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

HRID 451644노트

반응식

HRID 451644 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a6f3ab40f2f4892bc965e9898313c67
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487129B2

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