Triphenylphosphine → HCID 69731339, compound

HRID 1814379Notes

Reaction equation

HRID 1814379 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:25])(=[O:24])[NH:11][C@H:12]([C:21](=[O:23])[NH2:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([OH:26])[CH:5]=1.C1(O)C=CC=CC=1.[N:35]1[C:44]2[C:39](=[C:40]([CH2:45][CH2:46]O)[CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:25])[NH:11][C@H:12]([C:21](=[O:23])[NH2:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([O:26][CH2:46][CH2:45][C:40]2[CH:41]=[CH:42][CH:43]=[C:44]3[C:39]=2[CH:38]=[CH:37][CH:36]=[N:35]3)[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 69731384HCID 69731384, compound

Product 1

HCID 69731339HCID 69731339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenol 4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester (3.0 g, 7.50 mmol) in dry THF (50 mL) at 0° C. was added 2-quinolin-5-yl-ethanol (1.30 g, 7.5.0 mmol) and triphenyl phosphine (3.90 g, 15.0 mmol) then followed by dropwise addition of diethyl azodicarboxylate (2.40 mL, 15.0 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 12 h. The solvent was removed and the crude product was purified using silica gel flash chromatography (30% hexanes in EtOAc). 4-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-(2-quinolin-5-yl-ethoxy)-benzoic acid methyl ester was obtained (1.40 g, 33%) as an off white foam. MS m/z 556.2 (M−1).

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-5de55cc340544685b83d1bf05c51ecab
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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