Triphenylphosphine → HCID 57310114, compound

HRID 2185500Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][OH:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][O:19][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

N-tert-Butoxycarbonyl-D-homophenylalaninol (1.9 mmol), 2-hydroxyquinoline (2 mmol) and triphenylphosphine (2 mmol) were dissolved in dry THF (20 mL). The solution was cooled to 0° C. and diethyl azodicarboxylate (DEAD) (3.8 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 3 hr, then at room temperature for 16 hr at which time the solvent was evaporated under reduced pressure and the residue purified by chromatography on silica gel (100% CH2Cl2) to give the title compound (240 mg, 33%): 1H NMR (CDCl3) δ 1.46 (9H, s), 1.91-1.99 (2H, m), 2.76-2.81 (2H, m), 4.054.12 (1H, m), 4.51-4.53 (1H, m), 6.91-6.93 (1H, d), 7.19-7.30 (5H, m), 7.37-7.41 (1H, t), 7.61-7.65 (1H, t), 7.72-7.74 (1H, d), 7.82-7.84 (1H, d), 7.99-8.01 (1H, d); MS m/e 393 (100, M+1).

Workup

customat room temperature for 16 hr at which time the solvent was evaporated under reduced pressure
customthe residue purified by chromatography on silica gel (100% CH2Cl2)

Sources & evidence

ORD record: ord-3213b24c7a3f45488d54281961f76486
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399629B1

Reaction notes

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