Triphenylphosphine → 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid 3-tert-butoxycarbonylaminopropyl Ester

HRID 750189Notes

Reaction equation

HRID 750189 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:33])[N:12]1[C:21]([C:22]([OH:24])=[O:23])=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:31])[CH:18]=2)[C:13]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([O:57][C:58](=[O:64])[NH:59][CH2:60][CH2:61][CH2:62]O)([CH3:56])([CH3:55])[CH3:54].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:53]([O:57][C:58]([NH:59][CH2:60][CH2:61][CH2:62][O:23][C:22]([C:21]1[N:12]([N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH3:33])[C:13](=[O:32])[C:14]2[C:19]([C:20]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:18][C:17]([Cl:31])=[CH:16][CH:15]=2)=[O:24])=[O:64])([CH3:56])([CH3:55])[CH3:54]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 691557392-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 691562742-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid 3-tert-butoxycarbonylaminopropyl EsterYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (200 mg), triphenylphosphine (140 mg), (3-hydroxypropyl)carbamic acid tert-butyl ester (92 mg) and THF (4.0 ml), 0° C. with stirring, diethyl azodicarboxylate (90 μl) was added, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure preparative LC (hexane/ethyl acetate=5/1-3/2) to give the title compound (150 mg) as a colorless powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=5/1-3/2)

Sources & evidence

ORD record
ord-93cfd8540b5d4e61897787c5a8b4b6d9
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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