Naphthalene → HCID 66778987, compound

HRID 408984Notes

Reaction equation

C1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)C=CC=1.C1(O[NH:18][C@H:19]([C:23]([OH:25])=[O:24])[CH:20]([CH3:22])[CH3:21])CCCCC1.[P:26](Cl)(Cl)(=[O:38])[O:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C(Cl)[Cl:42]>>[Cl:42][C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:28]=1[O:27][P:26](=[N:18][C@@H:19]([CH:20]([CH3:22])[CH3:21])[C:23]([O:25][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)=[O:24])=[O:38]

Participants

Reactant 4

HCID 931Naphthalene

HCID 6344Dichloromethane

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 86662569HCID 86662569, compound

Product 1

HCID 66778987HCID 66778987, compoundYield 72%

Procedure

Using the general procedure for synthesizing naphthalene (amino acid ester) phosphorochloridates, the hydrochloride salt of cyclohexyloxy-L-valine (1.8 g), was combined with naphthalene-1-yl phosphorodichloridate (1.99 g), TEA (2.12 mL), and DCM (25 mL) to give (2S)-cyclohexyl 2-(chloro(naphthalen-1-yloxy)-phosphorylamino)-3-methylbutanoate in a 72% yield (2.34 g) as a pale yellow thick oil:

Sources & evidence

ORD record: ord-e93bf197ad654077be832775de67be25
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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