Triphenylphosphine → (S)-3-[4-acetylamino-2-((R)-2-indazol-1-yl-1-methyl-ethoxy)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814368Notes

Reaction equation

HRID 1814368 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[OH:30])(=[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:32]1([CH2:41][C@H:42]([CH3:44])O)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[N:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CO.O1CCCC1>[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[O:30][C@H:42]([CH3:44])[CH2:41][N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[N:33]1)(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69692589(S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterHCID 69731332HCID 69731332, compound

Product 1

HCID 69696519(S)-3-[4-acetylamino-2-((R)-2-indazol-1-yl-1-methyl-ethoxy)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.25 g (0.54 mmol) (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester, 0.096 g (0.54 mmol) (S)-2-indazol-1-yl-1-methyl-ethanol, 0.285 g (1.08 mmol) triphenylphosphine, and 40 mL dry tetrahydrofuran was stirred at room temperature. Diethyl azodicarboxylate 0.2 mL (1.08 mmol) was added dropwise and the resulting yellow solution was stirred 18 h at room temperature. TLC analysis indicated complete reaction. The reaction mixture was concentrated in vacuo to give a deep yellow oil. The product ether was purified over silica eluting with ethyl acetate to 9:1 ethyl acetate:methanol to yield 0.298 g (0.48 mmol, 89%) of (S)-3-[4-acetylamino-2-((R)-2-indazol-1-yl-1-methyl-ethoxy)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester as a colorless foam.

Workup

  1. stirringthe resulting yellow solution was stirred 18 h at room temperature
  2. customreaction
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a deep yellow oil
  5. customThe product ether was purified over silica eluting with ethyl acetate to 9:1 ethyl acetate

Sources & evidence

ORD record
ord-edfbad893ac74e3db2dbb6f12e6af461
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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