Water → HCID 89922662, compound

HRID 921904Notes

Reaction equation

HRID 921904 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([NH:20][C:21]1[C:22]([Cl:43])=[C:23]([CH:29]([OH:42])[CH2:30][N:31]([CH2:39][CH2:40]O)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:24]=[C:25]([C:27]#[N:28])[CH:26]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:13]([O:17][C:18]([NH:20][C:21]1[C:22]([Cl:43])=[C:23]([CH:29]2[O:42][CH2:40][CH2:39][N:31]([C:32]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:38])[CH2:30]2)[CH:24]=[C:25]([C:27]#[N:28])[CH:26]=1)=[O:19])([CH3:15])([CH3:14])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 131734947HCID 131734947, compound

Product 1

HCID 89922662HCID 89922662, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diethyl azodicarboxylate (203 μL, 1.28 mmol) was added to a solution of tert-butyl (2-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)-2-hydroxyethyl)(2-hydroxyethyl)carbamate (389 mg, 0.853 mmol) and triphenylphosphine (336 mg, 1.28 mmol) in dry toluene (9.0 mL) at room temperature. This was left stirring overnight. Water was added and the reaction was extracted with EtOAc. The organic phase was dried with sodium sulfate and the solvent was removed. Radial silica gel chromatography eluting with hexane containing 0 to 20% EtOAc afforded tert-butyl 2-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)morpholine-4-carboxylate (252 mg) as a colorless foam.

Workup

  1. waitThis was left
  2. extractionthe reaction was extracted with EtOAc
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customthe solvent was removed
  5. washRadial silica gel chromatography eluting with hexane containing 0 to 20% EtOAc

Sources & evidence

ORD record
ord-091a298c3403412d94f1b46654d0441b
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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