Dichloromethane → HCID 86662586, compound
Reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[P:30](Cl)(Cl)(=[O:42])[O:31][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.[Cl:52]CCl>>[Cl:52][C:33]1[CH:34]=[CH:35][C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:32]=1[O:31][P:30](=[N:12][C@@H:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:42]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-benzyl 2-amino-2-phenylacetate (1.11 mg, 2.69 mmol) was dissolved with the naphthalen-1-yl phosphorodichloridate (0.72 mg, 2.74 mmol) in 5 mL anhydrous dichloromethane. The solution was cooled down to −78° C. at which 0.76 mL of triethylamine (5.45 mmol) was added dropwise. Then the mixture was left stirring for 1 h at −78° C. and then 30 min at room temperature. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using Hexane/Ethyl acetate (1:1) as eluents, to provide (2S)-benzyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in 74% yield.
Workup
- additionwas added dropwise
- waitThen the mixture was left
- custom30 min
- customat room temperature
- customThe solvent was removed under reduced pressure
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-e9cc052d46414e45b8d59078319937cc
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759318B2
Reaction notes
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