N-Methylaniline → HCID 57264193, compound

HRID 1602986Notes

Reaction equation

HRID 1602986 reaction equation
C([O:4][C:5](=[O:35])[C@@H:6]([C:25]([S:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])([CH3:27])[CH3:26])[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])C=C.CNC1C=CC=CC=1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([O:17][C:14]2[CH:13]=[CH:12][C:11]([S:8]([NH:7][C@@H:6]([C:5]([OH:35])=[O:4])[C:25]([S:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])([CH3:26])[CH3:27])(=[O:10])=[O:9])=[CH:16][CH:15]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 7515N-MethylanilineHCID 56995255HCID 56995255, compound

Product 1

HCID 57264193HCID 57264193, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of N-[4-(4-fluorophenoxy)benzenesulfonyl]--S--[2-(methoxycarbonyl)ethyl]-D-penicillamine allyl ester (0.36 g, 0.687 mmol) in 5 mL of ethyl acetate was added N-methylaniline followed by Pd(PPh3)4 (16 mg, 0.014 mmol). After 3 hours, the solution was concentrated, and the residue was purified by chromatography on silica gel, eluting first with 1:1 ethyl acetate:hexane and then with 10% methanol in dichloromethane to give N-[4-(4-fluorophenoxy)benzenesulfonyl]--S--[2-(methoxycarbonyl)ethyl]-D-penicillamine as a white solid in 89% yield: mp 123-124° C.; 1H--NMR(CDCl3) δ 1.27 (s, 3H), 1.35 (s, 3H), 2.40-2.82 (m, 4H), 3.71 (s, 3H), 3.94 (d, 1H, J=11 Hz), 5.60 (d, 1H, J=11 Hz), 6.93-7.82 (m, 8H); FAB HRMS: expected (M+Cs)=618.0033. Found (M+Cs)=618.0038

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was purified by chromatography on silica gel
  3. washeluting first with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-6699969108414dc485384a3193a58fcd
Source dataset
uspto-grants-1999_11
Patent number
US05985900

Reaction notes

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