Dichloromethane → HCID 66778344, compound

HRID 408977Notes

Reaction equation

HRID 408977 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:22])[C:14]([O:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:15].[P:23](Cl)(Cl)(=[O:35])[O:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.C(Cl)[Cl:39]>>[Cl:39][C:26]1[CH:27]=[CH:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[O:24][P:23](=[N:12][C@@H:13]([CH3:22])[C:14]([O:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:15])=[O:35]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 85570p-ToluenesulfonateHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 44227191HCID 44227191, compound

Product 1

HCID 66778344HCID 66778344, compoundYield 65%

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the tosylate salt of (S)-cyclopentyl 2-aminopropanoate (4.00 g, 12.14 mmol), naphthalen-1-yl phosphorodichloridate (3.17 g, 12.14 mmol) and TEA (1.60 mL, 24.28 mmol) in 30 mL of dry DCM, were combined to give (2S)-cyclopentyl 2-(chloro(naphthalen-1-yloxy)-phosphorylamino)propanoate in 65% yield (3.01 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record
ord-81ffb11238854a869ece5b9682f839db
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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