Dichloromethane → (2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate

HRID 408971

반응식

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:20])[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15].[P:21](Cl)(Cl)(=[O:33])[O:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(Cl)[Cl:37]>>[Cl:37][C:24]1[CH:25]=[CH:26][C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]=1[O:22][P:21](=[N:12][C@@H:13]([CH3:20])[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15])=[O:33]

참가 물질

반응물 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 13742990Propyl (2S)-2-aminopropanoate

생성물 1

HCID 86662563(2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate수율 82%

실험 절차

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-propyl 2-aminopropanoate (2.00 g, 11.93 mmol), naphth-1-yl phosphorodichloridate (3.11 g, 11.93 mmol) and TEA (3.32 mL, 23.86 mmol) in 30 mL of dry DCM, were combined to give (2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 82% yield (3.50 g), as a clear, yellow, thick oil.

출처 및 근거

ORD 기록: ord-0d2b0f3b14104d6b988b39e944bffe61
출처 데이터셋: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08759318B2

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