Methanol → HCID 66616133, compound

HRID 2367067Notes

Reaction equation

HRID 2367067 reaction equation
[CH3:1][C:2]1([CH3:42])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:40])[C@@H:18]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N+:37]([O-:39])=[O:38])(=[O:30])=[O:29])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)[C:3]1=[O:41].CO.[C:45]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][C:2]1([CH3:42])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:40])[C@@H:18]([N:27]([CH3:45])[S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N+:37]([O-:39])=[O:38])(=[O:30])=[O:29])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:16]2)[C:3]1=[O:41]

Participants

7

Reactant 5

HCID 887MethanolHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66616121HCID 66616121, compound

Product 1

HCID 66616133HCID 66616133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (S)—N-(1-(4-(3,3-dimethyl-2-oxoindolin-1-yl)piperidin-1-yl)-1-oxo-4-phenylbutan-2-yl)-2-nitrobenzenesulfonamide (1.26 g, 2.13 mmol, EXAMPLE 73, Step 1), methanol (519 microL, 12.8 mmol), triphenylphosphine (1.12 g, 4.27 mmol) in tetrahydrofuran (10 mL) was added diethyl azodicarboxylate (2.2 mol/L toluene solution, 3.88 mL, 8.53 mmol) at room temperature. After 3 h, the mixture was concentrated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate, gradient) to give a mixture of the title compound and triphenylphosphineoxide (3.30 g).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, gradient)
  3. customto give

Sources & evidence

ORD record
ord-417b8931f8504c4e9a110ae6dd51ddd4
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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