Triphenylphosphine → HCID 66701209, compound

HRID 2062082Notes

Reaction equation

HRID 2062082 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[OH:23])=[O:11])([CH3:8])[CH2:6][CH3:7])[CH3:2].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([CH2:38]O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([CH2:38][O:23][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]([Cl:22])=[CH:21][C:12]=2[C:10](=[O:11])[NH:9][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])([CH3:8])[CH2:6][CH3:7])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine3×HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate3×HCID 58370173HCID 58370173, compound

Product 1

HCID 66701209HCID 66701209, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.95 g of 2-[(4-chloro-1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-butyric acid ethyl ester, 0.76 g 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester and 1.43 g triphenylphosphine in 30 mL of dry THF, 1.10 g of diisopropylazodicarboxylate were added. After 18 h at room temperature 1.43 g of triphenylphosphine and 1.10 g of diisopropylazodicarboxylate were added, and after 3 h again 1.43 g of triphenylphosphine and 1.10 g of diisopropylazodicarboxylate were added. After an additional 24 h the reaction was concentrated. After chromatography on silica (ethyl acetate/heptane) 1.17 g of 4-[4-chloro-2-(1-ethoxycarbonyl-1-methyl-propylcarbamoyl)-naphthalen-1-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester was obtained.

Workup

  1. concentrationAfter an additional 24 h the reaction was concentrated

Sources & evidence

ORD record
ord-b73c79b9294c4d19afaa4eda9a486208
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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