Triphenylphosphine → HCID 69692767, compound

HRID 1814387Notes

Reaction equation

HRID 1814387 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:22][C:21]=1[OH:35])(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[N:37]1[C:46]2[C:41](=[C:42]([CH2:47][CH2:48]O)[CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:36])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:22][C:21]=1[O:35][CH2:48][CH2:47][C:42]1[CH:43]=[CH:44][CH:45]=[C:46]2[C:41]=1[CH:40]=[CH:39][CH:38]=[N:37]2)(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 69692805HCID 69692805, compound

Product 1

HCID 69692767HCID 69692767, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.22 g (0.41 mmol), (S)-3-[4-(4-dimethylamino-butanoylamino)-2-hydroxy-benzensulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester, 0.079 g (0.41 mmol), 2-quinolin-5-yl-ethanol, 0.14 g (0.62 mmol) triphenylphosphine, and anhydrous methylene chloride (5 mL) was stirred at room temperature. Diethyl azodicarboxylate 0.1 mL (0.62 mmol) was added dropwise and the resulting orange solution was stirred at room temperature for 24 h. TLC analysis indicated complete reaction. The reaction mixture was concentrated in vacuo to give a deep yellow oil. The product was purified over silica eluting with 10% (8:1 EtOH/NH4OH): 90% methylene chloride to yield 0.115 g (0.17 mmol, 41%) of (S)-3-[4-(4-dimethylamino-butanoylamino)-2-(2-quinolin-5-yl-ethoxy) benzensulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester as a yellow oil. MS (APCI) m/z 685.5 (M−1).

Workup

  1. stirringthe resulting orange solution was stirred at room temperature for 24 h
  2. customreaction
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a deep yellow oil
  5. customThe product was purified over silica eluting with 10% (8:1 EtOH/NH4OH)

Sources & evidence

ORD record
ord-5d50e45fa4bc4ad09d629dcc1120facc
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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