Dichloromethane → HCID 86662568, compound

HRID 408980Notes

Reaction equation

HRID 408980 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].[P:23](Cl)(Cl)(=[O:31])[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(Cl)[Cl:35]>>[Cl:35][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][P:23](=[N:12][C@@H:13]([CH3:22])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])=[O:31]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 13038Phosphorodichloridic acid, phenyl esterHCID 85570p-ToluenesulfonateHCID 45086719HCID 45086719, compound

Product 1

HCID 86662568HCID 86662568, compound

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates, the tosylate salt of (S)-neopentyl 2-aminopropanoate (2.00 g, 6.03 mmol), phenyl phosphorodichloridate (0.90 mL, 12.06 mmol) and TEA (1.68 mL, 12.06 mmol) were combined in 66 mL of dry DCM. The product, (2S)-neopentyl 2-(chloro(phenoxy)phosphorylamino)propanoate was obtained as a clear, thick oil (1.91 g, 95%).

Workup

  1. customfor synthesizing naphthyl (amino acid ester) phosphorochloridates

Sources & evidence

ORD record
ord-45297587f5f542ed9f45aeef31f13068
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

Loading…