Dichloromethane → HCID 66779478, compound

HRID 408985Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[O:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:25])[C@@H:20]([NH2:24])[CH:21]([CH3:23])[CH3:22])[CH2:14][CH2:13]1.[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(N(CC)CC)C.[Cl:48]CCl>>[Cl:48][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:24][C@@H:20]([CH:21]([CH3:23])[CH3:22])[C:19]([O:18][CH:15]1[CH2:14][CH2:13][O:12][CH2:17][CH2:16]1)=[O:25])=[O:38]

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 61286353HCID 61286353, compound

Product 1

HCID 66779478HCID 66779478, compoundYield 67%

Procedure

Using the general procedure for synthesizing naphthylalene (amino acid ester) phosphorochloridates and tosylate salt of (S)-tetrahydro-2H-pyran-4-yl-2-amino-3-methylbutanoate (3.76 g, 10.0 mmol), naphthalene-1-yl phosphorodichloridate (2.62 g, 10.0 mmol), triethylamine (2.81 mL, 2.0 mmol) and dichloromethane (54 mL) were combined to give 2.89 g of desired (2S)-tetrahydro-2H-pyran-4-yl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-3-methylbutanoate as a pale yellow viscous oil in 67% yield.

Sources & evidence

ORD record: ord-d1382960968f479f82d41362dba4cc8a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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