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Phenyl isocyanate → Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

HRID 557273
Notes
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Reaction equation

HRID 557273 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:24]([CH2:27][CH2:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:31][CH:30]=1)([O-])=[O:25].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:25][N:24]=[C:27]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:41][CH:42]=3)[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridineHCID 59841574tert-butyl N-[(tert-butoxy)carbonyl]-N-(3-ethynylpyridin-2-yl)carbamate

Product 1

HCID 25114167Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

Under stirring at 50° C, to a solution of di-tert-butyl(3-ethinyl pyridin-2-yl)imidodicarbonate described in Preparation Example 3-1-1 (2.0 g), 2-(4-(2-nitro-ethyl)-benzyloxy) pyridine described in Preparation Example 1-3-4 (2.44 g), triethylamine (0.086 uL) and tetrahydrofuran (20 mL) was added phenyl isocyanate (2.8 mL) divided into four portions over 5.5 hours. After the additions were finished, stirring was carried out at 50° C for another two hours. NH-silica gel was added to the reaction solution, and the solvent was concentrated under a reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=3:1). The resulting solution was concentrated under a reduced pressure and purified by silica gel chromatography (heptane:ethyl acetate=3:1 then 2:1) to obtain the title compound (2.2 g).

Workup

  1. waitwas carried out at 50° C for another two hours
  2. additionNH-silica gel was added to the reaction solution
  3. concentrationthe solvent was concentrated under a reduced pressure
  4. customThe resulting residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=3:1)
  5. concentrationThe resulting solution was concentrated under a reduced pressure
  6. custompurified by silica gel chromatography (heptane

Sources & evidence

ORD record
ord-0ef0cdc571634133949460000f5162bc
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes