Triphenylphosphine → methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate

HRID 465622Notes

Reaction equation

HRID 465622 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[C:22]([O:26][NH:27][S:28]([CH:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]1=[C:38]=[O:39])(=[O:30])=[O:29])([CH3:25])([CH3:24])[CH3:23].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:22]([O:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[S:28]([CH:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]1=[C:38]=[O:39])(=[O:30])=[O:29])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10017284methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoateHCID 86746178HCID 86746178, compound

Product 1

HCID 86746177methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate (1.09 g 3.7 mmol), N-t-butoxy-carbonyl-p-chlorophenylsulfonamide (1.52 g, 5.2 mmol) and triphenylphosphine (1.92 g, 7.3 mmol) in methylene chloride (17 ml) is added dropwise diethyl azodicarboxylate (0.82 ml, 5.2 mmol). The reaction mixture is allowed to stir or 1 hour and the solvent is evaporated. The residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane to obtain methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate; IR (CH2Cl2): 1730, 1356, 1154 cm- 1.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-c01535285c094031aee9ef8e5fdd525f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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