Triphenylphosphine → HCID 54427559, compound

HRID 2416715Notes

Reaction equation

HRID 2416715 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N(C(OCC)=O)=NC(OCC)=O.O[C:26]1[CH:42]=[CH:41][C:29]2[CH2:30][CH:31]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:32](=[O:35])[NH:33][CH2:34][C:28]=2[CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:26]1[CH:42]=[CH:41][C:29]2[CH2:30][CH:31]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:32](=[O:35])[NH:33][CH2:34][C:28]=2[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 53769834HCID 53769834, compound

Product 1

HCID 54427559HCID 54427559, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(tert-butoxycarbonyl)amino]-1-propanol (0.14 g, 0.8 mmol) and diethyl azodicarboxylate (0.13 mL, 0.8 mmole) in anhydrous DMF (2 mL) was added dropwise to a solution of methyl (±)-8-hydroxy-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.10 g, 0.4 mmole) and triphenylphosphine (0.21 g, 0.8 mmol) in anhydrous DMF (1.4 mL) and dry THF (2 mL) at RT under argon. The resulting solution was stirred for 18 hr, then was concentrated under vacuum. Silica gel chromatography (1%-3% MeOH/CH2Cl2) gave the title compound (0.11 g): MS (ES) m/e 407.3 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-9191ed60335d42b38b445e5a3204eeac
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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