Hydrochloric Acid → HCID 86662587, compound

HRID 408997Notes

Reaction equation

HRID 408997 reaction equation
[ClH:1].[NH2:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH2:8][CH3:9])=[O:5].[P:16](Cl)(Cl)(=[O:28])[O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:1][C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]=1[O:17][P:16](=[N:2][C@@H:3]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH2:8][CH3:9])=[O:5])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 6997198HCID 6997198, compound

Product 1

HCID 86662587HCID 86662587, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates, the HCl salt of (S)-propyl 2-amino-2-phenylacetate (1 g), naphthalen-1-yl phosphorodichloridate (1.14 g), TEA (1.21 mL) and DCM (30 mL) were combined to give (2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in an 83% yield (1.51 g) as a pale yellow thick oil.

Workup

  1. customfor synthesizing naphthyl (aminoacid ester) phosphorochloridates

Sources & evidence

ORD record
ord-9356b71504184b149119a54ef61672f9
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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