p-Toluenesulfonate → HCID 86662567, compound

HRID 408979Notes

Reaction equation

HRID 408979 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:22])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].[Cl:23][P:24]([O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([C@H:38]([CH3:43])[C:39]([O:41][CH3:42])=[O:40])[CH:32]=[CH:31]2)(Cl)=[O:25]>C(Cl)Cl>[Cl:23][P:24]([O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([C@H:38]([CH3:43])[C:39]([O:41][CH3:42])=[O:40])[CH:32]=[CH:31]2)([NH:12][C@@H:13]([CH3:22])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])=[O:25]

Participants

5

Reactant 3

HCID 85570p-ToluenesulfonateHCID 45086719HCID 45086719, compoundHCID 86662556HCID 86662556, compound

Product 1

HCID 86662567HCID 86662567, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates and tosylate salt of (S)-neopentyl 2-aminopropanoate (1.0 g, 2.8 mmol), (S)-methyl 2-(6-(dichlorophosphoryloxy)naphthalen-2-yl)propanoate (990 mg, 2.8 mmol), TEA (0.8 mL, 5.6 mmol) and DCM (20 mL) were combined to give 1.13 g of desired (2S)-methyl 2-(6-(chloro((S)-1-(neopentyloxy)-1-oxopropan-2-ylamino)phosphoryloxy)naphthalen-2-yl)propanoate in 83% yield as a gummy syrup.

Sources & evidence

ORD record
ord-60d93383c45648098bfcffe53b5fd4b9
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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