Dichloromethane → HCID 86662574, compound

HRID 408988Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH2:12]([O:17][C:18](=[O:24])[C@@H:19]([NH2:23])[CH:20]([CH3:22])[CH3:21])[C:13]([CH3:16])([CH3:15])[CH3:14].[P:25](Cl)(Cl)(=[O:37])[O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][CH:31]=[CH:30]2.C(Cl)[Cl:41]>>[Cl:41][C:32]1[CH:31]=[CH:30][C:29]2[C:34](=[CH:35][CH:36]=[C:27]([O:26][P:25](=[N:23][C@@H:19]([CH:20]([CH3:21])[CH3:22])[C:18]([O:17][CH2:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:24])=[O:37])[CH:28]=2)[N:33]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 86662558HCID 86662558, compound

HCID 86662571HCID 86662571, compound

Product 1

HCID 86662574HCID 86662574, compound

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the tosylate salt of (S)-neopentyl-2-amino-3-methylbutanoate (1.9 g), quinolin-6-yl phosphorodichloridate (1.4 g), TEA (1.49 mL) and DCM (20 mL) were combined to give 600 mg of desired (2S)-neopentyl 2-(chloro(quinolin-6-yloxy)phosphorylamino)-3-methylbutanoate as thick oil.

Sources & evidence

ORD record: ord-73921d3d8ae041fe96313722ffe80521
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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