N,N,N',N'-Tetramethylazodicarboxamide → Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-[3-(tetrahydrofuran-3-yloxy)phenyl]pentanoate

HRID 2101223

Reaction equation

HRID 2101223 reaction equation
N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC.[O:26]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]1.[C:32]([O:36][C:37]([NH:39][C:40]1[N:45]=[CH:44][C:43]([CH2:46][CH:47]([CH:55]([S:65][CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=2)[CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60](O)[CH:59]=2)[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[CH:42][CH:41]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>C1(C)C=CC=CC=1>[C:32]([O:36][C:37]([NH:39][C:40]1[N:45]=[CH:44][C:43]([CH2:46][CH:47]([CH:55]([S:65][CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=2)[CH2:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[C:62]([O:31][CH:28]3[CH2:29][CH2:30][O:26][CH2:27]3)[CH:63]=2)[C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])=[CH:42][CH:41]=1)=[O:38])([CH3:33])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 99603-Furanol, tetrahydro-HCID 13831TributylphosphineHCID 69072041Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-hydroxyphenyl)-3-[(4-methoxybenzyl)thio]pentanoate

Product 1

HCID 69073200Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-[3-(tetrahydrofuran-3-yloxy)phenyl]pentanoateYield 44.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

1,1′-azobis(N,N-dimethylformamide)(134 mg, 0.78 mmol) was added to a solution of tri-n-butylphosphine (221 μL, 0.89 mmol) in toluene (2 mL). Tetrahydrofuran-3-ol (36 μL, 44 mmol) and tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-hydroxyphenyl)-3-[(4-methoxybenzyl)thio]pentanoate (154 mg, 0.25 mmol) was added sequentially. The reaction mixture was stirred for 12 h at 80° C. Toluene (100 mL) was added and the mixture was washed with brine, dried and concentrated. Flash chromatography (toluene/EtOAc, 100:0 to 70:30) gave tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-[3-(tetrahydrofuran-3-yloxy)phenyl]pentanoate (75 mg, 35%).

Workup

  1. washthe mixture was washed with brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e63b0239c61f48d596a027b78ddab03d
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Linked notes

Loading…