Triphenylphosphine → methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate

HRID 1786047Notes

Reaction equation

HRID 1786047 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][OH:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]([C@H:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[N:50]([C:57](=[O:65])[C:58]3[CH:63]=[CH:62][C:61](O)=[CH:60][CH:59]=3)[C@@H:49]([CH3:66])[CH2:48]2)[C:44](=[O:46])[CH3:45])=[CH:39][CH:38]=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[C:44]([N:43]([C:40]1[CH:39]=[CH:38][C:37]([Cl:36])=[CH:42][CH:41]=1)[C@H:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[N:50]([C:57]([C:58]2[CH:63]=[CH:62][C:61]([O:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[C:3]([O:2][CH3:1])=[O:16])=[CH:60][CH:59]=2)=[O:65])[C@@H:49]([CH3:66])[CH2:48]1)(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 68578092-Tert-butoxycarbonylamino-4-hydroxy-butyric acid methyl esterHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 68919251methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The ester was dissolved in 20 ml toluene at room temperature with PPh3 (0.94 g, 3.6 mmol), then added N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (0.31 g, 0.71 mmol) and stirred for 5 min. DEAD (0.626 g, 3.6 mmol) was added and the reaction was stirred for 18 h at room temperature. The reaction was concentrated and purified by silica gel chromatography (45% CH2Cl2/55% EtOAc) to afford crude methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate (0.47 g).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (45% CH2Cl2/55% EtOAc)

Sources & evidence

ORD record
ord-20811cdd034b4ad690392bfa44b54a5f
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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