Dichloromethane → (2R)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate

HRID 409002Notes

Reaction equation

HRID 409002 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[NH2:12][C@H:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].[P:28](Cl)(Cl)(=[O:41])[O:29]OC1C2C(=CC=CC=2)C=CC=1.C(N([CH2:49][CH3:50])CC)C.Cl[CH2:52][Cl:53]>>[Cl:53][C:52]1[CH:50]=[CH:49][C:10]2[C:8](=[CH:7][CH:6]=[CH:5][CH:11]=2)[C:9]=1[O:41][P:28](=[N:12][C@H:13]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])=[O:29]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 85570p-ToluenesulfonateHCID 86662591HCID 86662591, compoundHCID 86662592Naphthalen-1-yloxy phosphorodichloridate

Product 1

HCID 86662590(2R)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetateYield 58%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (R)-neopentyl 2-amino-2-phenylacetate (0.81 g, 2.08 mmol), naphthalen-1-yloxy phosphorodichloridate (0.54 g, 2.08 mmol), triethylamine (0.58 mL, 4.16 mmol) and dichloromethane (10 mL) were combined to give 0.51 g of desired (2R)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in 58% yield as pale yellow thick oil.

Sources & evidence

ORD record
ord-2310215f7779491e8192c9c55e65e24f
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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