Dichloromethane → HCID 86662570, compound

HRID 408986Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH:22]([CH3:24])[CH3:23])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].Cl[P:26]([O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C@H:40]([CH3:45])[C:41]([O:43][CH3:44])=[O:42])[CH:34]=[CH:33]2)(Cl)=[O:27].C(Cl)[Cl:47]>>[Cl:47][C:31]1[C:32]2[C:37](=[CH:36][C:35]([C@H:40]([CH3:45])[C:41]([O:43][CH3:44])=[O:42])=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[O:29][P:26](=[N:12][C@@H:13]([CH:22]([CH3:24])[CH3:23])[C:14]([O:16][CH2:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:15])=[O:27]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 86662556HCID 86662556, compound

HCID 86662571HCID 86662571, compound

Product 1

HCID 86662570HCID 86662570, compound

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the tosylate salt of (S)-neopentyl 2-amino-3-methylbutanoate (776 mg), and (S)-methyl 2-(6-(dichlorophosphoryloxy)naphthalen-2-yl)propanoate (750 mg), TEA (0.6 mL) and DCM (15 mL) were combined to give 580 mg of desired (2S)-neopentyl 2-(chloro(6-((S)-1-methoxy-1-oxopropan-2-yl)naphthalen-2-yloxy)phosphorylamino)-3-methylbutanoate as gummy solid.

Sources & evidence

ORD record: ord-208f16021d384d59b20c5f7ec40102d9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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